Author: Jessica.F

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C15H23BrO

In a 300 mL reactor sufficiently dried and purged with argon, 0.46 g (18.8 mmol) of magnesium pieces were charged and vigorously stirred for 30 minutes while heating under reduced pressure. After cooling to room temperature, a piece of iodine and 20 mL of tetrahydrofuran were charged and stirred. To this solution, J.Am. Chem. Soc. 2006, 128, 16486. A 30 mL dilute solution of 5.17 g (17.3 mmol) of 1-bromo-3,5-di-tert-butyl-4-methoxybenzene synthesized by the method described above was added dropwise (1.0 mL added)After that, the mixture was heated to reflux until the color of iodine disappeared with a drier, and after the start of the reaction, the remaining droplets were dropped), and after completion of the dropwise addition, the mixture was heated to reflux in an oil bath at 80 C. for 1 hour.The reaction solution was cooled to -78 C., 2.20 mL (19.8 mmol) of trimethoxyborane was slowly added, and stirring was continued for 19 hours while slowly returning to room temperature. An aqueous solution of 1.0 M hydrochloric acid was added, the solubles were extracted with di-iso-propyl ether, and the obtained fraction was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated to give a residue, which contains 3.38 g (15.0 mmol) of the compound (A-4a) obtained in Synthesis Example 4-1, tripotassium phosphate 7. 34 g (34.6 mmol), 0.03 g (0.15 mmol) of palladium acetate, 2-dicyclohexylphosphino-2 ‘, 6’-dimethoxybiphenyl (0.10 g (0.23 mmol) of S-Phos), 35 mL of tetrahydrofuran and 7 mL of distilled water were charged, and the mixture was heated under reflux for 2 hours in an oil bath. The reaction solution is cooled to room temperature, a saturated aqueous ammonium chloride solution is added, and the soluble matter is extracted with n-hexane and ethyl acetate to obtainThe fraction was washed with brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the desired product represented by the following formula (A-4b) (hereinafter referred to as compound (A-4b)) Is 5.44 g (yield 99%) were obtained.

According to the analysis of related databases, 1516-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H13BrO

Compound 38E: Methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)- 1 /-/-pyrrole-2-carboxylate.A mixture of methyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrole-2- carboxylate (Compound 38F, 600 mg, 2.39 mmol) and 1-bromo-3-benzyloxypropane (575 mg, 2.51 mmol) in DMF (2.19 mL) was charged with cesium carbonate (778 mg, 2.39 mmol). The reaction mixture was allowed to stir at 70 °C for 16 hrs. The reaction mixture was diluted with water and then extracted with EtOAc (2x). The organic layer was washed with water (2x), brine (1 x), dried over Na2S04, filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash.(R). Rf system [0–> 4percent Ethanol in DCM] to afford 442mg of the title compound (46percent). 1H NMR (400 MHz, CD3OD) delta 7.26 – 7.37 (m, 5H), 7.25 (d, J = 1 .8 Hz, 1 H), 7.17 (d, J = 1.8 Hz, 1 H), 4.45 (s, 2H), 4.42 (t, J = 6.8 Hz, 2H), 3.78 (s, 3H), 3.38 (t, J = 5.9 Hz, 2H), 2.01 (t, J = 6.2 Hz, 2H), 1 .31 (s, 12H). MS (ESI): m/z 440.59 [M+H]+. UPLC: tR = 1.60 min (UPLC-TOF: polar_2 min).

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; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (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. 452-08-4, name is 2-Bromo-4-fluoro-1-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 452-08-4

106 ml of 2.5 M butyllithium in hexane are added dropwise at -20 C. to a solution of 2-bromo-4-fluoro-1-methoxy-benzene (50 g) in 1 l of pentane, and stirred for 15 min at -10 C., then cooled to -30 C. Then trimethylborate (30 ml) is added, stirred 30 min at 0 C., cooled to -10 C., followed by the addition of a 32% peracetic solution (103 ml) over 45 min keeping the temperature to below -5 C. and stirring 30 min at 0 C. The mixture is cooled to -10 C., 150 ml of a saturated NaHSO3 solution are added, stirred 1 h at AT, then after adding water, neutralizing with 330 g of NaHCO3 and decanting the pentane, the aqueous layer is extracted with DCM. The organic layer is washed with sodium hydroxide, the aqueous layer is acidified with a concentrated HCl solution, extracted with DCM and the organic layer is dried over MgSO4, filtered and concentrated to dryness. 27.1 g of desired product are obtained.

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; CEREP; US2009/233910; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)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 18800-30-1, Computed Properties of C8H8Br2O

EXAMPLE 1 A mixture of 2.8 parts of 1-bromo-4-(2-bromoethoxy)benzene, 5 parts of cis-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3-H1,2,4-triazol-3-one, 0.7 parts of potassium hydroxide and 100 parts of dimethyl sulfoxide was stirred for 4 hours at room temperature. The reaction mixture was poured into water. The product was extracted with dichloromethane. The extract was subsequently washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel usinq a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2′-oxybispropane. The product was filtered off and recrystallized from methylbenzene, yielding 5.2 parts (79%) of cis-2-[2-(4-bromophenoxy)ethyl]-4-[4-[ 4-[4-[[2-(2,4-dichlorophenyl)-2-(1 H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one; mp. 143.3 C. (compound 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-(2-bromoethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica, N.V.; US4791111; (1988); A;,
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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 588-96-5 as follows. Recommanded Product: p-Bromophenetole

To a solution of 2R-allyl-3S-hydroxy-succinic acid diisopropylester (4.79 g, 18.5 MMOL), 4-bromo phenetole (3.19 ML, 22.2 mmol, 1.2 eq. ) and NEt3 (6.22 ML, 44.6 mmol, 2.4 eq. ) in CH3CN (40 ml), was added a sonicated (for 2 min) suspension of P (O-TOL) 3 (0.57 g, 2.22 mmol, 0.1 eq. ) and Pd (OAC) 2 (209 mg, 5%) in CH3CN (5 ML). The reaction mixture was heated to reflux for 2 hrs. CH3CN was removed under vacuo. The crude was extracted with AcOEt (3 X 200 ML), washed with water (50 ML) and with brine (50 ML). A purification by flash chromatography afforded the desired 2R- [3- (4-ETHOXY-PHENYL)-ALLYL]-3S- hydroxy-succinic acid diisopropyl ester (5.92 g, 84% yield).

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERNALIS (OXFORD) LIMITED; LABORATOIRES SERONO S.A.; WO2005/19194; (2005); A1;,
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Synthetic Route of 16618-68-1,Some common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-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)..Prep aration o f .intermediate 34; A solution of butanoyl chloride (0.0292 mol) in DCM (10ml) was added dropwise to a solution of 3-bromo-5-methyloxybenzenamine (0.0292 mol) and Et3N (0.035 mol) in DCM (50ml) at 5C under N2 flow. The mixture was stirred at room temperature for 1 hour. K2CO3 10% was added and the organic layer was decanted, dried (MgSO4), filtered off and evaporated till dryness, yielding 8 g (100%) of intermediate 34.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-methoxyaniline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/53373; (2009); 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. 22483-09-6, name is 2,2-Dimethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C4H11NO2

(a) Ethyl N-(2,2-dimethoxyethyl)-carbamate 214 g (2 mol) of ethyl chloroformate are added dropwise to 214 g (2 mol) of aminoacetaldehyde dimethyl acetal in 1 l of toluene and 90 g of NaOH in 500 ml of water at 10 C. The mixture is stirred at room temperature for a further 2 hours and the aqueous phase is separated off, saturated with sodium chloride and extracted with toluene. The toluene solutions are dried over magnesium sulphate and concentrated and the residue is distilled. Yield: 338 g (95.4% of theory) Boiling point: 60 C./0.03 mbar

The synthetic route of 22483-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US4990517; (1991); A;,
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Reference of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-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.

At 5 C., a solution of bromine (9.8 mL, 192.5 mmol, 1.1 eq) in dichloromethane (120 mL) was added slowly to a dichloromethane solution (240 mL) of 4-bromo-2-methoxyaniline (35.35 g, 175 mmol) under vigorous stirring. The reaction mixture was kept at this temperature for 2 h. After the completion monitored by TLC, the reaction mixture was poured into ice water and extracted with ethyl acetate (3*200 mL). The organic layer was combined, washed with brine (3*50 mL) and dried over sodium sulfate. Then the reaction mixture was purified by flash column chromatography (ethyl acetate/hexanes (v/v)=5/95). The product (40.3 g, yield=82%) was obtained as a red liquid. 1H NMR (600 MHz, CDCl3) delta 7.20 (d, J=1.9 Hz, 1H), 6.84 (d, J=1.8 Hz, 1H), 4.21 (s, 2H), 3.86 (s, 3H). LRMS m/z 280.0 [M+H]+.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Cierpicki, Tomasz; Grembecka, Jolanta; Huang, Huang; Zari, Sergi; Cho, Hyo Je; Potopnyk, Mykhaylo; Dudkin, Sergeii; Chen, Wenbing; Adam, Yassir; Howard, Christina; Kim, EunGi; US2019/183865; (2019); A1;,
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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 6298-96-0 as follows. SDS of cas: 6298-96-0

To a 250 mL RBF was added (S)-1-(4-methoxyphenyl)ethanamine (6.39 g, 42.3 mmol), 1-(3- methylpyridin-2-yl)ethanone (6 g, 44.4 mmol), DCM (Volume: 106 ml) and STAB-H (17.92 g, 85 mmol) at rt and the reaction was stirred for 24h. The reaction was quenched by the addition of 1N NaOH until a pH of 8 was achieved. The phases were separated and the organic layer was treated with 1N NaOH until pH 11 was observed. The DCM layer was dried with MgSO4 filtered and concentrated to an oily residue. The residue was purified via combiflash to separate the diastereomers (~4:1 by crude NMR, 80g column 10-30% gradient over 40 min). 1H NMR (400 MHz, CDCl3): delta= 8.45 (d, J= 4.8 Hz, 1H), 7.34 (d, J= 7.6 Hz, 1H), 7.13 (d, J= 8.5 Hz, 2H), 7.04 (dd, J= 7.8, 4.6 Hz, 1H), 6.82 (d, J= 9.2 Hz, 2H), 3.79 (s, 3H), 3.74 (q, J= 6.0 Hz, 1H), 3.27 (q, J= 5.9 Hz, 1H), 1.24 (d, J= 6.3 Hz, 3H), 1.20 (d, J= 6.3 Hz, 3H); LC/MS 75% MeOH in H2O over 3 minutes, rt = 0.480 at 254 nM, MS (+) 271.2

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); 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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H17NO2

General procedure: 3.2. Reaction of Wang Resin 1 with Trichloroacetonitrile and Fmoc-amino Alcohol (Resin 2)Wang resin 1 (1 mmol/g loading, 1 g) was suspended in 10 mL of anhydrous DCM, then 1.5 mL oftrichloroacetonitrile was added, and the resin was left in a freezer for 30 min. Next, a solution of 100 Lof DBU in 2 mL of anhydrous DCM was added, and the slurry was shaken for 1 h. The resin waswashed with anhydrous DCM (3) and anhydrous THF (3). The solution of Fmoc-amino alcohol(3 mmol) in 10 mL of anhydrous THF was added to the resin, followed by the dropwise addition of63 L of a solution of BF3Et2O, and the slurry was shaken for 30 min. Resin 2 was washed THF (3),MeOH (3), and DCM (5). A sample of the resin was washed with MeOH (3) and dried, and10 mg was cleaved with 50% TFA for 30 min, and the product quantified (Fmoc absorbance at 300 nm).Typical loading was between 0.35-0.50 mmol/g.3.3. Acylation with a-Bromocarboxylic Acids (Resins 3 And 13)Resin 2 (1 g) was washed with DCM and DMF, Fmoc was deprotected with 50% piperidine inDMF for 15 min, and the resin was washed with DMF (3) and DCM (5). Reaction of the resinwith a solution of -bromocarboxylic acid (5 mmol) in 10 mL of DCM was carried out in a syringewith a frit, and DIC (2.5 mmol, 386 L) was added. After 5 min, DIU was filtered, and the solutionwas transferred to the syringe with resin 1 and shaken for 1 h. When bromoacetic acid was used,DIEA (2.5 mmol, 436 L) was also added. Then, the resin was washed with DCM (3)._ 3.4. Reaction with Amino-aldehyde Dialkyl Acetal and N-Derivatization (Resin 4)Resin 3 (1 g) was washed with DMF (3), a solution of amino-aldehyde dialkyl acetal (10 mmol)and DIEA (10 mmol, 1.74 mL) in 10 mL of DMF was added, and the slurry was shaken for 2 h.An analytical sample was taken for analysis, reacted with 0.5 M Fmoc-OSu in DCM for 1 h and cleavedwith 50% TFA for 30 min.Resin from the previous step was split into four 250 mg portions, which were washedwith reaction solvent: DCM for sulfonamides (Ns-Cl, Tos-Cl) (1 mmol) and DMSO for 4-fluoro-3-nitrobenzotrifluoride (1 mmol). Then, 3 mL of the reaction solvent and DIEA (1.8 mmol, 174 L) wasadded, and the slurry was shaken for 2 h (in the case of sulfonamides) or overnight (in the case of4-trifluoromethyl-2-nitroaryl). Resin 4 was washed with the reaction solvent (3) and then DCM (3).A sample for analysis was reacted with 0.5 M Fmoc-OSu in DCM for 1 h and cleaved with 50% TFA for30 min.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gimenez-Navarro, Vanesa; Krch?ak, Viktor; Molecules; vol. 23; 5; (2018);,
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