Author: Jessica.F

Related Products of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, methyl (2S)-5-amino-6-bromo-2-methyl-1,2,3,4-tetrahydroquinoline-1-carboxylate (300 mg, 1.00mmol, Intermediate 1) was dissolved in toluene (5 mL). Then 3,3- diethoxypropan-1-amine (885 mg, 6.01mmol), 3rd Generation BrettPhos precatalyst (91 mg, 0.10mmol), BrettPhos (108 mg, 0.20mmol) and sodium tert-butoxide (289 mg, 3.01mmol) were added successively. The resulting solution was stirred for 2 h at 110oC under nitrogen atmosphere. The reaction mixture was cooled and the resulting solids were filtered out. The filtrate was concentrated under vacuum. The residue was subjected to purification by FCC eluting with ethyl acetate/petroleum ether (2:1). This afforded the title compound (240 mg, 62%) as a yellow oil. MS: (ES, m/z): 366 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; SCHILLER, Shawn E.R.; HERBERTZ, Torsten; LI, Hongbin; GRAVES, Bradford; MISCHKE, Steven; WEST, Angela V.; ERICSSON, Anna; DOWNING, Jennifer R.; (484 pag.)WO2019/55877; (2019); A1;,
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Reference of 3401-47-6, A common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[Step 1] Synthesis of 1-(2-Fluorophenyl)-2-methoxynaphthalene Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80 C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2012/165550; (2012); A1;,
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Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 645-36-3

2,2-Diethoxyethylamine (470 muL, 3.23 mmol) was added to a suspension of pyrimidine 9 (0.63 g, 2.67 mmol) in i-PrOH (30 mL), and the mixture was stirred at r.t. until the starting compound has dissolved. Et3N (560 muL, 4.0 mmol) was then added and the mixture was stirred for a further 45 min. H2O (50 mL) was added and the product was extracted with CH2Cl2 (2 × 50 mL). The organic layers were combined, washed with H2O (2 × 20 mL), dried (Na2SO4), and concentrated. The residue was purified by flash chromatography(silica gel, CH2Cl2; Rf = 0.42) to give a yellow solid; yield: 0.61 g(69%); mp 65.5-67.5 C.IR (KBr): 3380 (NH) cm-1. 1H NMR (300 MHz, CDCl3): delta = 1.27 (t, J = 6.9 Hz, 6 H, 2 × CH3),2.55 (s, 3 H, SCH3), 3.60 (dq, 2J = 9.3 Hz, 3J = 6.9 Hz, 2 H,2 × CHAHBCH3), 3.72-3.83 (m, 4 H, NCH2 and 2 × CHAHBCH3),4.09 (s, 3 H, OCH3), 4.68 (t, J = 5.4 Hz, 1 H, OCH), 8.84 (br s, 1 H,NH).13C NMR (75 MHz, CDCl3): delta = 14.8, 15.6, 44.3, 55.7, 63.2, 100.5,113.5, 156.6, 163.8, 174.6.Anal. Calcd for C12H20N4O5S: C, 43.36; H, 6.07. Found: C, 43.68;H, 6.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
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Electric Literature of 450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The solution of anisole of formula 2 (Scheme 6) (61 .5 g, 0.3 mol) in 1 ,2-dichloroethane (DCE) (600 mL) was cooled to -10 C and AICI3 was added in portions, maintaining the temperature below 2 C. The solution was then cooled to -5 C and acetyl chloride (56 mL, 0.79 mol) was added dropwise maintaining the internal temperature below 5 C. The reaction mixture was aged for 1 hour at 0 C. At this time HPLC showed no more starting material. The reaction mixture was quenched into ice (600 g) at a rate such that the internal temperature remained below 20 C. The resulting mixture was extracted with EtOAc (400 mL) and the organic phase then washed with 1 HCL (400 mL), saturated NaHC03 (400 mL) and brine (200 mL), dried over Na2S0 and filtered. The solvent was removed under reduced pressure to give acetophenon of formula 3 (Scheme 6) as a white solid (74.0 g, 100%): mp 1 13-1 17 C; H NMR (CDCI3) 5 2.59 (d, J = 5.1 Hz, 3H), 3.95 (s, 3H), 6.64 (d, J = 12.5 Hz, 1 H), 8.13 (d, J = 7.9 Hz, 1 H).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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Application of 116557-46-1,Some common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 3-bromo-2-methoxyaniline (3 g), 3-carboxyphenylboronic acid (2.94 g), bis(triphenylphosphine)palladium(II)chloride [PdCl2(PPh3)2] (0.30 g) and potassium carbonate (5.2 g) in ethanol (100 mL) and water (20 mL) was heated to about reflux temperature and stirred for about 28 hours. The hot mixture was filtered to remove the catalyst. The clear filtrate was concentrated under vacuum. To the residue, water (50 mL) and methanol (50 mL) was added, acidified to pH 3-5 using hydrochloric acid and stirred for about 30 minutes at about room temperature. The slurry was filtered, washed with n-hexane (50 mL) and dried in an oven at about 55 C. to about 60 C. for about 12 hours. Yield: 1.8 g 1H NMR (300 MHz in DMSO-d6): delta 8.08 (s, 1H), 7.89-7.92 (d, 1H), 7.73-7.75 (d, 1H), 7.51-7.56 (t, 1H), 6.87-6.92 (t, 1H), 6.72-6.74 (d, 1H), 6.50-6.53 (d, 1H), 3.27 (s, 3H)

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glenmark Generics Limited; Upadhye, Bhargav Krishnaji; Jagadale, Shivaji Eknath; Soni, Mukesh; US2015/87845; (2015); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene

Outside the glovebox, a 100 mL Schlenk flask equipped with a magnetic stir bar was charged with commercially available 3-(trifluoromethyl)benzoic acid (BFA) (3.09 g, 16.2 mmol) and bromoanisole BrMIP (3.60 g, 14.6 mmol). The flask was transferred to glovebox (%O2 ?0.005) and Pd(OAc)2 (157 mg, 5 mol %), n-butyl-di-1-adamantylphosphine (530 mg, 10 mol %), Cs2CO3 (11.92 g, 36.6 mmol) and powdered dry molecular sieves 3 A (1.0 g) were added. The flask was closed with the rubber septum and taken out of the glovebox. Anhydrous DMF degassed with nitrogen was added through the septum and the obtained mixture was first stirred at room temperature for 1 h under the positive pressure of nitrogen, and then placed in a preheated oil bath (145 C) for 24 h. The reaction mixture was cooled to room temperature and quenched with 2M HCl (100 mL). Ethylacetate (50 mL) was added and the resulting suspension was stirred for 15 min, filtered through a pad of celite and the layers were cut. The water layer was extracted with ethyl acetate (50 mL) and all organic phases were combined, washed with brine (50 mL) and evaporated under reduced pressure to obtain a yellow oil. The crude product was purified by column chromatography to give 4′-fluoro-5′-Isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acid as a colorless oil (3.11g, 60%). 1H NMR (DMSO-d6) delta 0.95 (d, J = 8.0, 6H), 3.36 (s, 1H), 626 (d, J =12.0, 1H), 6.83 (d, J = 8.0, 1H), 7.03 (d, J = 8.0, 1H), 7.25 (m, 1H), 7.74 (s, 1H).

The synthetic route of 944317-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2468736; (2012); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 134364-69-5, name is 2,3-Difluoroanisole, A new synthetic method of this compound is introduced below., Recommanded Product: 2,3-Difluoroanisole

Example 1; 2′-Chloro-2,5-difluoro-4-methoxybenzophenone Aluminum chloride (92.54 g, 694 mmol) was transferred to a bottle (in a glove bag under dry N2), then to the reaction flask. Dichloromethane (600 mL) was added via syringe and the suspension cooled to 0 C. (ice-H2O bath). 2-Chlorobenzoyl chloride (88.2 mL, 121.45 g, 694 mmol) was added via syringe at 0-5 C. over 13 min. The addition funnel was rinsed with 10 mL dichloromethane. The difluoroanisole (77.8 mL, 100.0 g, 694 mmol) was then added dropwise via syringe at 0-5 C. over 13 min. The resulting yellow solution was stirred at 0-5 C. for 3.5 h (until the bath warmed) then at 20-25 C. for 14 h.The solution is poured over 600 g ice in a 2 L round bottom flask. Dichloromethane (80 mL) was used to complete the transfer. The layers were separated and the aqueous layer was extracted with 80 mL dichloromethane. The combined organic layers were transferred to a 1 L flask (with paddle stirrer) for distillation under dry N2. The dichloromethane is then replaced by n-heptane. At a bath temperature of 55-65 C., the head temperature is 35-38 C. and the pot temperature climbs to as high as 52 C. The pot solution is cooled and n-heptane (400 mL) is added. The distillation is continued. At a bath temperature of 100 C., the head temperature climbs from 55 to 75 C. and pot temperature climbs to as high as 83 C. before stopping the distillation (collected 767 mL total distillate). The pot suspension is now two phases, colorless on top and yellow on bottom. The suspension is allowed to cool to 50 C. and stirred at 200 rpm for 1 h. The suspension is allowed to cool to 40 C. and stirred at 200 rpm for 1 h. The suspension is allowed to cool to 30 C. and stirred at 200 rpm for 1 h. The 30 C. suspension is then cooled to 0-5 C. and stirred for 30 min. The precipitate is suction filtered (600 ml coarse sintered glass funnel), washed with 100 mL n-heptane at 0 C., and air dried 17 h at 25 C. to afford 181.23 g (92.4%) of light yellow solid.Recrystallization from hexanes provides colorless crystals, m.p. 84-85 C.; 500 MHz 1H NMR (CDCl3) delta 7.56 (dd, J=6.5 Hz, J=11.5 Hz, 1H), 7.43-7.39 (m, 3H), 7.38-7.34 (m, 1H), 6.65 (dd, J=6.6 Hz, J=11.5 Hz, 1H), 3.94 (s, 3H); 125 MHz 13C NMR (CDCl3) delta 190.2, 159.2 (dd, J=2 Hz, J=253 Hz), 153.9, 148.7 (dd, J=3 Hz, J=244 Hz), 140.0, 131.7, 131.21, 131.19, 130.2, 129.08, 129.07, 127.1, 117.5 (dd, J=3 Hz, J=21 Hz), 101.7 (dd, J=2 Hz, 29 Hz), 56.9; IR (KBr) 3057, 2986, 2941, 1663, 1653, 1620, 1519, 1443, 1420, 1360 cm-1. Elem. Anal. Calcd for C14H9ClF2O2: C, 59.49; H, 3.21; Cl, 12.54; F, 13.44. Found: C, 59.49; H, 3.13.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Roche Colorado Corporation; US2009/203901; (2009); A1;,
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Synthetic Route of 24988-36-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 24988-36-1 as follows.

Into a 200-mL three-neck flask were put 7.1 g (24 mmol) of 1,5-dibromo-2,4-dimethoxybenzene, 2.8 g (20 mmol) of 2-fluorophenylboronic acid, 12 mL of toluene, 12 mL of diethylene glycol dimethyl ether, and 50 mL of a sodium carbonate aqueous solution (2 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 0.55 g (0.48 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at the same temperature for 3 hours. After the mixture was cooled down to the room temperature, 4.5 g (32 mmol) of 2-fluorophenylboronic acid and 0.12 g (0.29 mmol) of 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl were added to the mixture and then the mixture was degassed under reduced pressure. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. again. After that, 30 mg (0.13 mmol) of palladium(II) acetate was add ed to the mixture, and stirring was performed at the same temperature for 4 hours. After the stirring, the mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a brown oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was subjected to a gradient to change from hexane to chloroform gradually) to give 7.2 g (22 mmol) of a target pale yellow oily substance at a yield of 92%. A synthesis scheme of the above synthesis method is shown in (B-2) below.

According to the analysis of related databases, 24988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Kawakami, Sachiko; Ishiguro, Yoshimi; Takahashi, Tatsuyoshi; Hamada, Takao; Seo, Hiromi; Seo, Satoshi; (113 pag.)US9997725; (2018); B2;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7664-66-6, name is 4-Isopropoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H13NO

General procedure: 2-Hydroxynaphthalene-1-carboxylic acid or 1-hydroxynaphthalene-2-carboxylic acid (5.30 mmol) and appropriate alkoxyaniline (5.30 mmol) were suspended in 30 mL of dry chlorobenzene. Phosphorous trichloride (2.65 mmol) was added dropwise, and reacting mixture was heated in the microwave reactor for 15 min at 130 C using infrared flask-surface control of temperature. Solvent was evaporated in vacuum; residue solid was washed with 2M HCl and crystallized from aqueous ethanol. If necessary, column chromatography was used for further purification (mobile phase DCM:MeOH 19:1).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gonec, Tomas; Pospisilova, Sarka; Kauerova, Tereza; Kos, Jiri; Dohanosova, Jana; Oravec, Michal; Kollar, Peter; Coffey, Aidan; Liptaj, Tibor; Cizek, Alois; Jampilek, Josef; Molecules; vol. 21; 8; (2016);,
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Application of 54149-17-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthetic procedures of the zwitterionic compounds reported in previously published papers (Kuroda, K.; Satria, H.; Miyamura, K.; Tsuge, Y.; Ninomiya, K.; Takahashi, K. Journal of the American Chemical Society 2017, 139, 16052-16055; Yoshizawa-Fujita, M.; Tamura, T.; Takeoka, Y.; Rikukawa, M. Chemical Communications 2011, 47, 2345-2347) were used for this Example. Briefly, 0.2 mol sodium hydride was suspended in tetrahydrofuran (THF) under argon gas. Imidazole (0.1 mol), which was dissolved in 30 mL THF, was added dropwise to the sodium hydride solution. After stirring for 24 h at room temperature, 1-bromo-2-(2-methoxyethoxy)ethane (0.1 mol) was added to the solution. The resulting suspension was filtered after stirring for 6 h at 70 C. to remove the white precipitate. The solvent was removed by rotary evaporation to yield the crude product. The product was further purified by distillation under reduced pressure. A fraction was collected at 105 C. under reduced pressure to obtain 1-(2-(2-methoxyethoxy)ethyl)-1H-imidazole (OE2im). OE2im (0.1 mol) was subsequently dissolved in 40 mL acetonitrile. 1,4-butanesultone (0.1 mol) was added dropwise to the solution under a nitrogen atmosphere. The mixture was then refluxed for 40 h. The solvent was then removed by rotary evaporation. The residue was washed several times with diethyl ether by decantation followed by drying of the product under vacuum at 50 C. for 24 h to obtain IL 1, 3-(1-(2-Methoxyethyl)-1H-imidazol-3-ium-3-yl)butane-1-sulfonate (OE2imC4S) as a colorless viscous liquid. The zwitterionic compounds IL 2, 3-(1-octyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate (C8imC3S), and IL 4, 3-(1-octyl-1H-imidazol-3-ium-3-yl)butane-1-sulfonate (C8imC4S), were prepared in similar procedure using octylimidazole with 1,3-propanesultone or 1,4-butanesultone.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Iowa State University Research Foundation, Inc.; Anderson, Jared L.; Kuroda, Kosuke; Nan, He; (27 pag.)US2019/360979; (2019); A1;,
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