Tag: M.W=200-300

Synthetic Route of 29578-39-0, 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 29578-39-0 as follows.

A mixture of 1-bromo-3-fluoro-5-methoxy-benzene (80 g, 0.39 mol), TEA (118 g, 1.17 mol), Pd(OAc)2 (16 g, 20%) and DPPP (16 g, 20%) in MeOH (800 mL) is stirred under a 3 Mpa atmosphere of CO for 2 days. The mixture is filtered and the filtrate is concentrated under reduced pressure. The crude is purified by flash silica gel chromatography to afford compound D-9-1 (42 g, 59% yield).

According to the analysis of related databases, 29578-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; BRENNEMAN, Jehrod Burnett; GINN, John David; HOPKINS, Tamara Denise; LOWE, MIchael D.; SARKO, Christopher Ronald; WESTBROOK, John A.; YU, Maolin; ZHANG, Zhonghua; (233 pag.)US2016/24059; (2016); A1;,
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Reference 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: NaN3 (0.42 g, 6.5 mmol) was added to a stirred solution of 1-bromo-4-(3-bromopropoxy)benzene (1.47 g, 5 mmol) in DMSO (25 mL). The mixture was stirred for 12 h at room temperature, diluted with H2O (50 mL), and extracted by EtOAc (50 mL .x. 3). The organic layer was separated, dried with Na2SO4, and concentrated under reduced pressure. The residue was white solid and reacted to the next step without further purification. The synthetic method for the compound 5b was similar to the synthesis of compound 5a.

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; Wang, Shengzheng; Jin, Gang; Wang, Wenya; Zhu, Lingjian; Zhang, Yongqiang; Dong, Guoqiang; Liu, Yang; Zhuang, Chunlin; Miao, Zhenyuan; Yao, Jianzhong; Zhang, Wannian; Sheng, Chunquan; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 292 – 299;,
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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. 19056-40-7, name is 4-Bromo-3-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-3-methoxyaniline

Intermediate Example Int26.013-(4-bromo-3-methoxyphenyl)-1 ,3-oxazolidin-2-oneTo a stirred solution of 4-Bromo-3-methoxy-aniline (10.0 g) in acetonitrile (176 mL) was added Hiinig Base (25 mL) and 2-chloroethyl chloroformate (10.6 g). The mixture was stirred at room temperature for 0.5 h . The solvent was removed in vaccuum. The residue was dissolved in tetrahydrofurane (250 mL), and potassium tert.-butoxide (16.2 g) was added. The mixture was stirred at room temperature for 2 h. The solvent was removed in vaccuum. The residue was dissolved in ethyl acetate and the mixture was washed with water and with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave a compound that was crystallized from ethanol. Yield: 7.7 g of the title compound. The mother liquor was concentrated in vaccuum and aminophase-silica-gel chromatography gave a solid that was recrystallized from ethanol to give further 2.3 g of the title compound.1H-NMR (300MHz, CHLOROFORM-d): delta [ppm]= 4.00 – 4.10 (m, 2H), 4.45 – 4.55 (m, 2H), 6.66 (dd, 1 H), 7.49 (d, 1 H), 7.63 (d, 1 H).

The synthetic route of 19056-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philip; WENGNER, Antje Margret; BRIEM, Hans; HOLTON, Simon; SIEMEISTER, Gerhard; PRECHTL, Stefan; KOPPITZ, Marcus; STOeCKIGT, Detlef; PRIEN, Olaf; WO2011/157688; (2011); A1;,
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Electric Literature of 1663-61-2, A common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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.

b. l-Azidoethyl-2,4-dibenzoylmannoseTo a 1.0L, 3-neck flask containing a stir bar, nitrogen inlet and 300 mL of anhydrous acetonitrile was added 25 gm 1-azidoethylmannose (100.4 mmole), and 50 mL triethyl orthobenzoate (220 mmole, 2.2 equiv.). The resulting slurry was stirred at room temperature and 0.8mL (10 mmole) trifluoroacetic acid (TFA) was added neat. The solution cleared within 10 minutes and stirring was continued for an additional two hours , then 25 mL of 10percent aqueous TFA was added and stirring was continued for an additional 2 hours to hydrolyze the intermediate to the ester isomers. The solvent was evaporated under vacuum to a viscous oil, which was triturated with 50 mL DCM and again evaporated to a viscous oil.Toluene (70 mL) was added to the residue and the viscous solution was seeded with 2,4- dibenzoylazidoethylmannose. A fine precipitate formed within 15 minutes and stirring was continued overnight at room temperature. The resulting heavy suspension was set in the freezer for 2-4 hours, then filtered and the solid washed with ice cold toluene (2×10 mL). The solid was air dried to a constant weight to give 21 gm (TY 22.85 gm (at) 50percent isomeric purity) of -95percent isomeric purity. The product was taken into 40 mL toluene, stirred for 1 hour and then set in the freezer for an additional 2 hours. The solid was filtered and washed (2×10 mL) with ice cold toluene and air dried to a constant weight to give 18.5 gm of the single isomer product 2,4- dibenzoylazidoethylmannose in 83percent yield. The mother liquors contained the undesired isomer and a small amount of the desired isomer. The reaction was monitored by TLC: SG (Hexane/Ethyl Acetate 7/3) Starting Material Rf 0.0, orthoester intermediate Rf 0.9. (Hexane/Ethyl Acetate: 8/2) SM Rf 0.8, desired isomer Rf 0.4, un-desired isomer Rf 0.2. 1H NMR 300MHz (CDCl3) delta 8.12(t, 4H), 7.66(t, 2H), 7.5(m, 4H), 5.56(t, IH), 5.48(m, IH), 5.14(m, IH), 4.5(dd, IH), 4.0(m, 2H), 3.8(m, 3H), 3.56(m, IH), 3.44(m, IH).

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMARTCELLS, INC.; ZION, Todd, C.; LANCASTER, Thomas, M.; WO2010/88261; (2010); A1;,
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Application of 261762-35-0,Some common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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.

3,4-Difluoro-5-methoxybenzoic acid (72a) (0327) The title compound was prepared by reaction of 5-bromo-1,2-difluoro-3-methoxybenzene (1.03 g, 4.62 mmol, 1.0 equiv) and magnesium (112 mg, 4.61 mmol, 1.0 equiv) and iodine (2 mg) in 13 ml diethylether under reflux for 2 h. Carbon dioxide was bubbled through the solution at 10 C. until all solvent (13 ml) was evaporated two times. The crude product was dissolved in 10 mL THF and carbon dioxide was bubbled through the solution for additional 1 h. The reaction was quenched with 1 M HCl, extracted with ethyl acetate, dried with magnesium sulfate and concentrated under reduced pressure to afford the crude product, which was purified by flash chromatography; yield: 31% (265 mg). 1H NMR (300 MHz, MeOH-d4) delta 7.65-7.45 (m, 2H), 3.99 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1,2-difluoro-3-methoxybenzene, its application will become more common.

Reference:
Patent; ELEXOPHARM GMBH; Hartmann, Rolf; Frotscher, Martin; Ahmed, Ahmed Saad Abdelsamie; Bey, Emmanuel; van Koppen, Chris J.; Oberwinkler-Marchais, Sandrine; Boerger, Carsten; Siebenbuerger, Lorenz; Hernandez Olmos, Victor; (72 pag.)US2016/318895; (2016); 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 887581-09-1 as follows. category: ethers-buliding-blocks

Step 3: tert-butyl (2-bromo-5-methoxybenzyl)carbamate To a solution of 1-(2-bromo-5-methoxyphenyl)methanamine (3.2 mmol) in DCM (15 mL) was added BOC2O (3.2 mmol). The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was purified by column chromatography to give tert-butyl (2-bromo-5-methoxybenzyl)carbamate (3.1 mmol, 95%).

According to the analysis of related databases, 887581-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 261762-35-0,Some common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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.

3,4-Difluoro-5-methoxybenzoic acid (72a) (0327) The title compound was prepared by reaction of 5-bromo-1,2-difluoro-3-methoxybenzene (1.03 g, 4.62 mmol, 1.0 equiv) and magnesium (112 mg, 4.61 mmol, 1.0 equiv) and iodine (2 mg) in 13 ml diethylether under reflux for 2 h. Carbon dioxide was bubbled through the solution at 10 C. until all solvent (13 ml) was evaporated two times. The crude product was dissolved in 10 mL THF and carbon dioxide was bubbled through the solution for additional 1 h. The reaction was quenched with 1 M HCl, extracted with ethyl acetate, dried with magnesium sulfate and concentrated under reduced pressure to afford the crude product, which was purified by flash chromatography; yield: 31% (265 mg). 1H NMR (300 MHz, MeOH-d4) delta 7.65-7.45 (m, 2H), 3.99 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1,2-difluoro-3-methoxybenzene, its application will become more common.

Reference:
Patent; ELEXOPHARM GMBH; Hartmann, Rolf; Frotscher, Martin; Ahmed, Ahmed Saad Abdelsamie; Bey, Emmanuel; van Koppen, Chris J.; Oberwinkler-Marchais, Sandrine; Boerger, Carsten; Siebenbuerger, Lorenz; Hernandez Olmos, Victor; (72 pag.)US2016/318895; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 887581-09-1 as follows. category: ethers-buliding-blocks

Step 3: tert-butyl (2-bromo-5-methoxybenzyl)carbamate To a solution of 1-(2-bromo-5-methoxyphenyl)methanamine (3.2 mmol) in DCM (15 mL) was added BOC2O (3.2 mmol). The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was purified by column chromatography to give tert-butyl (2-bromo-5-methoxybenzyl)carbamate (3.1 mmol, 95%).

According to the analysis of related databases, 887581-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 103291-07-2, These common heterocyclic compound, 103291-07-2, name is 4-Bromo-1-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.

[0413] A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (1.2 g, 8.1 mmol), 4-bromo- l-fluoro-2-methoxy-benzene (1.8 g, 8.9 mmol), Pd2(dba)3 (0.74 g, 0.81 mmol), Xaniphos (0.93 g, 1.6 mmol) and cesium carbonate (7.88 g, 24.2 mmol) were suspended in dioxane (60 mL) and heated at reflux under the argon atmosphere for 5 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford the title compound (0.3 g, 14%) as a beige solid.

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
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Synthetic Route of 19056-41-8, The chemical industry reduces the impact on the environment during synthesis 19056-41-8, name is 3-Bromo-4-methoxyaniline, I believe this compound will play a more active role in future production and life.

2-Amino-4-chloro-3′-methoxybenzophenone. In a flame-dried round bottom flask 4-chloroanthranilic acid N-methoxy-N-methylamide (4.58 g, 21.3 mmol) and m-bromoanisidine (4.02 g, 21.5 g) were dissolved in THF (185 mL) and the resulting solution was cooled to -78 C. With vigorous stirring, 2 equiv of nBuLi in hexanes (26.9 mL, 1.6 M, 43.0 mmol) was added dropwise by a syringe pump at 0.6 mL/min. After 20 min, 40 mL of 1 N hydrochloric acid was carefully added, the mixture was extracted with ethyl acetate (300 mL), and the ethyl acetate was washed with water (100 mL) and brine (100 mL), dried over sodium sulfate and concentrated in vacuo. Flash chromatography with hexanes/ethyl acetate (95:5, then 75:25) afforded 3.75 g (67% yield) of 2-amino-3′-methoxybenzophenone as a yellow oil. 1 H NMR (50 MHz, CDCL3): delta 3.83 (s,3), 6.17 (b, 2), 6.55 (dd, 1, J=2.0, 8.5), 6.72 (d, 1, J=2.0), 7.06 (dd, 1, J=2.6, 8.5), 7.13 (m, 2), 7.35 (t, 1, J=7.8), 7.39 (d, 1, J=8.5).

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, 3-Bromo-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Board of Regents, The University of Texas System; The Regents of the University of California; US6100254; (2000); A;,
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