Tag: M.W=200-300

Some common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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. Recommanded Product: 944317-92-4

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 944317-92-4, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 20469-65-2

To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 C. was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 C. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction was then cooled to 0 C. and BBr3 (7.2 ml, 76 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction was again cooled to 0 C. and BBr3 (3.6 ml, 38 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hours. The mixture was then poured slowly onto ice. When the ice melted, DCM (200 ml) was added and the layers separated. The aqueous was extracted with EtOAc (500 ml) and the layers separated. The combined organics were passed through a through a hydrophobic frit and concentrated. The residue was purified via flash chromatography (ISCO Combiflash Rf, 220 g column, 0-100% ethyl acetate/hexanes) to give the title compound as a yellow oil (19.5 g, 70% purity). MS (m/z) 189.0 (M+).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HAMMOND, Marlys; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (190 pag.)US2016/340328; (2016); A1;,
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Electric Literature of 886762-08-9, 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 5-bromo-2-(trifluoromethoxy)aniline (2 g, 7.8 mmol), K2CO3 (2.7 g, 19.5 mmol), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (50% in THF, 4.4 mL, 15.6 mmol) in dioxane (60 mL) was degassed for 20 min with N2. PdCl2(dppf)- CH2Cl2 (319 mg, 0.39 mmol) was added and the mixture was further degassed for 10 min then heated to 100 oC for 1 h. The reaction mixture was cooled to rt, filtered through a pad of celite, concentrated, and purified by chromatography (EA/hexane) to provide 1.49 g (74%) of Intermediate 44A. LCMS [m/z] calculated for C8H8F3NO: 191.1 found 192.2[M+H]+, tR=4.22 min (Method 4).

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; YEAGER, Adam; TURNBULL, Philip; ZHANG, Lin; FAN, Junhua; TAMIYA, Junko; STEINBERG, Marcos; FOWLER, Tom; BENELKEBIR, Hanae; PASCERI, Raffaele; IEVA, Maria; GRANT, Kevan; TRAN, Yang; (403 pag.)WO2018/45246; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 60876-70-2, Quality Control of 1-Bromo-4-(tert-butoxy)benzene

Synthesis of (4-tert-butoxy-phenylethynylVtrimethyl-silane (2). A 20 mL microwave tube was charged with a mixture of 1 -bromo-4-tert- butoxybenzene 1 (1.0 g, 4.36 mmol), PdCl2(dppf) (71 mg, 0.087 mmol), CuI (33 mg,0.174 mmol), DIPA (0.924 mL, 6.55 mmol), and THF (15 mL). Tube was backfilled with nitrogen, sealed, and irradiated in a microwave reactor (max. power 250W) at 100C for 5 min. Solution was diluted with water (200 mL) and extracted with EtOAc (3 x 80 mL). Combined organic layers were washed with water (1 x 100 mL) and brine (1 x 80 mL), dried (Na2SO4), filtered and concentrated in vacuo. Crude product was purified by normal phase flash chromatography (40 g SiO2, 0-30% EtO Ac/Hex) to provide the desired compound 2 (488 mg, 45%) as a clear colorless oil. LC-MS: [M+H]+= Not observed; Ret. Time (Method A) 7.87 min; 1H NMR (250 MHz, CDCl3) delta 0.2 (s, 9H), 1.3 (s, 9H), 6.9 (d, 2H), 7.4 (d, 2H).

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-4-(tert-butoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHAOGEN, INC.; WO2008/154642; (2008); A2;,
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Reference of 112970-44-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 112970-44-2 name is 2-Bromo-3-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A dry round-bottom flask with a reflux condenser was charged with 2-bromo-3-methoxyanilin (1.00 g, 4.95 mmol), KHMDS(32 mg, 0.16 mmol, 0.03 eq), BrettPhos Pd G1 Methyl-t-Butyl Ether adduct (118 mg, 0.15 mmol, 0.03 eq) and Cs2CO3 (3.22 g,9.88 mmol, 2.0 eq). The system was sealed by a rubber septum before air was removed under reduced pressure and replaced by argon (repeated 3 times). Anhydrous toluene (20 mL) was transferred to the flask and the resulting orange colored suspension gradually warmed up to reflux and left stirring for 24 h. The heating was removed and the crude mixture was cooled to reach rt . Thereaction mixture was filtered through a funnel of Celite and undissolved material washed with DCM until no yellow solution came through the funnel. The resulting crude mixture was dry-loadedon silica and purified by flash column chromatography on silicagel (1:7 EtOAc/DCM as eluent) affording 468 mg (79%) of the yellow solid. Rf: 0.51 (100% EtOAc). 1H NMR (400 MHz, CDCl3) d7.99 (dd, J = 8.9, 1.1 Hz, 2H), 7.74 (dd, J = 8.9, 7.6 Hz, 2H), 7.09(dd, J = 7.6, 1.1 Hz, 2H), 4.17 (s, 6H). 13C NMR (101 MHz, CDCl3) d155.1, 143.2, 137.0, 130.3, 122.2, 107.0, 56.6. HRMS (EI): Exactmass calculated for C14H12N2O2: 240.0899, found 240.0894(1.8 ppm). 1H- and 13C NMR data are in accordance with published literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-3-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Article; Viktorsson, Elvar Oern; Melling Gr°the, Bendik; Aesoy, Reidun; Sabir, Misbah; Snellingen, Simen; Prandina, Anthony; H°gmoen ?strand, Ove Alexander; Bonge-Hansen, Tore; D°skeland, Stein Ove; Herfindal, Lars; Rongved, Pal; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2285 – 2293;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 29578-39-0, category: ethers-buliding-blocks

A solution of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1 H-pyrazol-4-ylboronic acid (41 mg, 0.083 mmol), 1-bromo-3- fluoro-5-methoxybenzene (20 mg, 0.10 mmol), Pd(PPh3)4 (10 mg, 0.0083 mmol), Na2003 (44 mg, 0.42 mmol) in degassed 1,4-dioxane and H20 (4:1, 1.7 mL) was heated at 85 C for 18 hours. LiOH (10 mg, 0.42 mmol) was added and the reaction was heated at 95 O under microwave radiation for 30 mm. i N HCI (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of ammonium formate) (60 to 80%). The product was lyophylised to give the title compound (16 mg, 0.028 mmol, 34%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) O 8.21 (d, J= 1.8 Hz, 1H), 8.03 (dd, J= 8.5, 1.8 Hz, 1 H), 7.75 (d, J = 8.5 Hz, 1 H), 6.94 -6.89 (m, 2H), 6.86 (d, J = 11.5 Hz, 1 H), 3.80 (5, 3H),3.35 (sept, J = 6.7 Hz, 1H), 2.32 (5, 3H), 1.24 (d, J= 6.7 Hz, 6H); MS (mlz): 552.1 [M+1].

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-3-fluoro-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
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Electric Literature of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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.

General procedure: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole (L1): A solution of 3,5-dimethyl-1H-pyrazole (0.30 g, 3.2 mmol) in DMF/THF (v/v = 1:1, 12 mL) was added to a suspension of NaH (0.15 g, 6.4 mmol) in DMF/THF (v/v = 2:1, 15 mL) and stirred at 60 °C for 2 h. Then, the resulting solution was added under stirring to a solution of 3-bromopropyl phenyl ether (0.70 g, 3.2 mmol) in DMF (7 mL). The mixture was allowed to stir for 24 h at 60 °C, cooled, and treated cautiously with H2O (5 mL) to decompose excess NaH. The solvents were then evaporated under reduced pressure. The residue was extracted with ethyl acetate (3 * 15 mL), washed with H2O (2 * 15 mL). The organic phase was dried over MgSO4 and filtered, before the solvent was evaporated under reduced pressure. After workup and purification by chromatographic column on silica gel (hexane/ethyl acetate, 90:10), L1 was obtained as a colorless oil (0.47 g, 64percent).

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

Reference:
Article; Ulbrich, Ana H.D.P.S.; Campedelli, Roberta R.; Milani, Jorge L. Sonego; Santos, Joao H.Z. Dos; Casagrande, Osvaldo De L.; Applied Catalysis A: General; vol. 453; (2013); p. 280 – 286;,
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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. 873980-68-8, name is 4-Bromo-2-methoxy-5-methylaniline, A new synthetic method of this compound is introduced below., Computed Properties of C8H10BrNO

Preparation 40: 2-methoxy-5-methyl-4-(1 -methyl-1 A7-pyrazol-4-yl)aniline To a solution of 4-bromo-2-methoxy-5-methylaniline (Preparation 39, 350 mg, 1 .620 mmol) in EtOH (2.5 mL), toluene (2.5 mL) and water (2.5 mL) was added 1 -methylpyrazole-4- boronic acid pinacol ester (404 mg, 1 .944 mmol), sodium carbonate (343 mg, 3.24 mmol) and Pd(PPh3)4 (225 mg, 0.194 mmol). The reaction mixture was heated to 80C for 2.5 hours, under nitrogen. The reaction mixture was cooled to room temperature and diluted with EtOAc (30 mL), washed with water (30 mL) and brine (30 mL), dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-5% MeOH in DCM to give the title compound (140 mg, 36%). 1 H NMR (500 MHz, CDCI3): delta 7.56 (d, J = 0.5 Hz, 1 H), 7.39 (s, 1 H), 6.75 (s, 1 H), 6.63 (s, 1 H), 3.96 (s, 3H), 3.86 (s, 3H), 3.76 (br s, 2H), 2.27 (s, 3H). LCMS (ESI) Rt = 1 .13 minutes MS m/z 218.30 [M+H]+

The synthetic route of 873980-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; SOLANKI, Savade; WOODWARD, Hannah; NAUD, Sebastian; BAVETSIAS, Vassilios; SHELDRAKE, Peter; INNOCENTI, Paolo; CHEUNG, Jack; ATRASH, Butrus; WO2014/37750; (2014); A1;,
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Reference of 6358-77-6, These common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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.

A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); A1;,
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588-96-5, name is p-Bromophenetole, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of p-Bromophenetole

Preparation Example 3 Synthesis of 1-bromo-3-(4-ethoxybenzyl)benzene; A 2.6 M n-butylithium hexane solution (5.8 mL) was added to a mixture of 4-bromophenetole (2.87 g, 0.0143 mol) and tetrahydrofuran (30 mL) at -78C. After the mixture was stirred for 0.5 hours, a tetrahydrofuran (15 mL) solution of 3-bromobenzaldehyde (2.65 g, 0.0143 mol) was added, and further stirred for 15 minutes to warm the reaction mixture to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=7:1 to 5:1) to obtain colorless oily (3-bromophenyl)(4-ethoxyphenyl)methanol (3.94 g, 90%). Then, Et3SiH (4.09 mL, 0.0256 mol) and BF3·Et2O (1.47 mL, 0.0116 mol) were added sequentially to a chloroform (22 mL) solution of (3-bromophenyl)(4-ethoxyphenyl)methanol (3.92 g, 0.0128 mol) at -60C. After stirred for one hour, the reaction solution was warmed to room temperature. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain a colorless oily title compound (2.84 g, 76%). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.40 (t, J=7.0 Hz, 3 H) 3.88 (s, 2 H) 4.01 (q, J=7.0 Hz, 2 H) 6.83 (d, J=8.9 Hz, 2 H) 7.07 (d, J=8.9 Hz, 2 H) 7.09 – 7.18 (m, 2 H) 7.29 – 7.34 (m, 2 H).

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1845095; (2007); A1;,
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