Month: June 2021

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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H6BrFO

Example 2; 2-(4-Fluoro-3-methoxvphenvlV4,4,5.5-tetramethvl-1.3,2-dioxaborolane; Anhydrous 1,2-dimethoxy ethane (12 mL) was added to 4-bromo-l-fluoro-2- methoxybenzene (1.02 g, 5.0 mmol), tris(dibenzylideneaceton)dipalladium (0) (228 mg, 0.25 mmol), tricyclohexylphosphine (209 mg, 0.75 mmol), potassium acetate (732 mg, 7.5 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-l,3,2-dioxaborolane (1.14 g, 4.5 mmol) and 5 the resulting mixture was irradiated in a microwave at 150 C for 1 h. When cooled to ambient temperature the mixture was filtered and the solvent was evaporated in vacuo to give the crude product: MS (EI) m/z 252 [M+*].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 103291-07-2.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/145569; (2007); A1;,
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Application of 148583-65-7, These common heterocyclic compound, 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, 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.

Example 1 5-Ethyl-N-(4-fluoro-2-isopropoxy^henyl)pyrrolo[3,2-d]pyrimidin^ 2-isopropoxy-4-fluoroaniine (55mg, 0.33mmol), Intermediate 2 (54mg, 0.30mmol), 4M HCi in dioxane (0.1ml) and IPA (2ml) were heated in the microwave at 140C for 20 min. The mixture was concentrated and purified by preparative LCMS to give a white solid (41 mg, 44%); 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.43 (d, J=6.0 Hz, 6 H), 1.61 (t, J=7.3 Hz, 3 H), 4.45 (q, J=7.3 Hz, 2 H), 4.68 (spt, J=6.0 Hz, 1 H), 6.60 (d, J=3.2 Hz, 1 H), 6.69 (dd, J=10.0, 2.7 Hz, 1 H), 6.75 (td, J=8.7, 2.7 Hz, 1 H), 7.24 (d, J=3.2 Hz, 1 H), 7.58 (br. s, 1 H), 8.54 (s, 1 H), 8.75 (dd, J=8.9, 6.2 Hz, 1 H); LC-MS (ESI): (MH+) 315.2

The synthetic route of 148583-65-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; WINTER-HOLT, Jon James; MCIVER, Edward Giles; LEWIS, Stephen; OSBORNE, Joanne; (106 pag.)WO2017/85483; (2017); A1;,
Ether – Wikipedia,
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Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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. Quality Control of 1-Bromo-3-methoxypropane

To a 50 Ljacket reactor containing 5-bromo-2-methoxy-phenol (1.185 kg, 5.78mo1), 1- bromo-3-methoxy-propane (1.028 kg, 6.52 mol) and acetonitrile (12 L) was added anhydrousK2C03 (1.212 kg, 8.68 mol) in one portion at room temperature. The resulting mixture was heated to 75 C and the agitation was maintained for 16 hours. The reaction mixture was slowly cooled to room temperature, and to the mixture was added water (6 L) and EA (8 L). The organic phase was separated and washed with 5% brine (6 L) again. The organic layer was filtered through a Na2504 pad, and concentrated under reduced pressure to give 1.6 Kg of 4-bromo- 1-methoxy-2-(3-methoxypropoxy)benzene as a light brown solid, which was used directly in thenext step without further purification. The yield was 98 %, the purity was 99.3 %, and MS obsd.(ESIj [(M+H)i: 275.1. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.84 – 2.04 (m, 2 H) 3.25 (s, 3H) 3.33 (s, 1 H) 3.46 (t, J=6.27 Hz, 2 H) 4.01 (t, J=6.27 Hz, 2 H) 5.58 – 9.80 (m, 3 H) 5.58 – 9.80(m, 3 H) 6.92 (d, J=8.53 Hz, 1 H) 7.04 – 7.13 (m, 2 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36865-41-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DU, Zhengming; WANG, Lin; (43 pag.)WO2017/16960; (2017); A1;,
Ether – Wikipedia,
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These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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. Safety of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

A stirred suspension of methyl 4-(3,5-dichloro-4-hydroxybenzamido)benzoate (1) (Synthesis 9) (100 mg, 294 mumol) in toluene (2 mL) was heated at 80 C. until homogenous. The resultant solution was treated with 1,1-di-tert-butoxy-N,N-dimethylmethanamine (141 muL, 588 mumol) and the mixture heated at 80 C. for 3 h, and then at RT for 18 h. Additional 1,1-di-tert-butoxy-N,N-dimethylmethanamine (141 muL, 588 mumol) was added and mixture was heated at 80 C. for 5 h. The reaction mixture was cooled to RT and solvent was removed in vacuo. The residue was diluted with water and extracted with Et2O. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was partially purified by silica gel chromatography (12 g, 0-50% EtOAc in isohexane) to afford methyl 4-(4-(tert-butoxy)-3,5-dichlorobenzamido)benzoate (2) (82 mg, 71%). The material was used in the next step without further purification.

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 437-83-2,Some common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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.

Hydrobromic acid (48% in water, 140 mL) is added slowly to an aliquot of 11 (14. 33 g, 101. 5 mmol) cooled to 0 C. The resulting solid is broken up with a glass rod and stirred vigorously at 0 C for 10 min. A solution of sodium nitrite (7. 40g, 107. 2 mmol) in water (50 mL) is added slowly (-1. 5 h) to the stirred slurry containing 3-fluoro-2- methoxyphenylamine and hydrobromic acid, maintaining the temperature of the reaction mixture below 5 C. A purple solution of cuprous bromide (9. 62 g, 67. 1 mmol) in hydrobromic acid (48% in water, 50 mL) is added dropwise to the reaction mixture, maintaining the temperature of the reaction mixture below 5 C. The resulting reaction mixture is heated at 60 C until the evolution of gas ceases (-2. 5 h). The reaction mixture is cooled to room temperature, and the product extracted with diethyl ether (6 x 150 mL). The combined organic extracts are washed with brine (3 x 150 mL), dried over magnesium sulfate, and evaporated under reduced pressure to give 1-BROMO-3-FLUORO-2-METHOXYBENZENE as a brown oil. This product is of sufficient purity (295% by NMR spectroscopy) to use directly in the next synthetic STEP. 1H NMR (CDCl3) : No.3. 95 (d, JH-F= 1.5 Hz, 3H, OCH3), 6. 88 (apparent t OF D, JH-H = 8. 0 Hz, JH-F = 5. 5 Hz, 1H, H-5), 7. 04 (ddd, JH-F = 10. 5 Hz, JH-H = 8. 0 HZ, JH-H = 1. 5 Hz, 1H, H-4), 7. 30 (d of apparent T, JH-H = 8. 0 Hz, JH-H = 1. 5 Hz, JH-F = 1. 5 Hz, 1H, H-6). I9F {LH} NMR (CDCl3) : S-127. 7 (s). 13C {IH} NMR (CDCl3) : 1561. 4 (d, JC-F= 5. 0 Hz, OCH3), 116. 2 (d, JC-F = 19. 5 Hz, C-4), 117. 7 (D, JC-F = 3. 0 Hz, C-1), 124. 5 (d, JC-F = 8. 0 Hz, C-5), 128. 5 (D, JC-F = 3. 5 Hz, C-6), 145. 7 (d, Jc-F = 12. 5 Hz, C-2), 156. 2 (d, JC-F = 250. 5 Hz, C-3).

The synthetic route of 437-83-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WO2005/19228; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 104-92-7, name is 1-Bromo-4-methoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-methoxybenzene

General procedure: A mixture of Ni(cod)2 (0.050 mmol), SIPr·HCl (0.050 mmol),KOt-Bu (0.050 mmol), and CPME was stirred at 100 C for 30min. To this was added NaOAc (0.85 mmol), aryl bromide 1(0.50 mmol), and N-TMS-carbazole 2 (0.65 mmol). The reactionmixture was quenched with H2O. The aqueous layer wasextracted with Et2O and washed with brine. The combinedorganic layers were dried over anhydrous MgSO4. After concentrationin vacuo, the residue was purified by flash chromatographyon silica gel or preparative TLC to afford N-aryl-carbazoles 3.

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:
Article; Minami, Yasunori; Komiyama, Takeshi; Shimizu, Kenta; Uno, Shu-Ichi; Hiyama, Tamejiro; Goto, Osamu; Ikehira, Hideyuki; Synlett; vol. 28; 18; (2017); p. 2407 – 2410;,
Ether – Wikipedia,
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Synthetic Route of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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 (1,3-dioxoisoindolin-2-yl)potassium (10.0 g, 53.9 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (37.5 g, 161 mmol) in acetone (250 mL) was stirred at 60 C. for 12 h. On completion, the reaction mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography to give the title compound (12.0 g, 74% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.91-7.84 (m, 2H), 7.77-7.72 (m, 2H), 3.96-3.90 (m, 2H), 384-377 (m, 4H), 3.42 (t, J==6.0 Hz, 21-).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-(2-bromoethoxy)ethane, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Ether – Wikipedia,
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Application of 2398-37-0,Some common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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 round-bottomed flask was charged acetyl chloride (4.20g, 53.56mmol, leq), AICI3 (7.13g, 53.56mmol, leq), and carbon disulfide (80mL). To the mixture was added dropwise a solution of 3-bromoanisole (9.75g, 52.13mmol) in carbon disulfide (20mL) and stirred for 16 h. The resulting solution was diluted with ice water (l OOmL) and extracted with CH2G12 (50mLx3). The extracts were washed with H20, brine, and IN NaOH (30mL). The organic layer was dried over MgS04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes = 1 :10) to afford the title compound (6.2g, 51%).1H NMR (300MHz, CDC13) delta 7.48(dd, J = 8.4Hz, 1,2Hz, 1H), 7.04(brs. 1H), 6.76(dd, 1H), 3.74(s, 3H), 2.52(s, 3H)

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

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; HEO, Jung Nyoung; BAE, Myung-Ae; KIM, Nack Jeong; CHANG, Sung Youn; KANG, Namsook; YOO, Sung Eun; HWANG, Eun Sook; WO2011/30955; (2011); A1;,
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Reference of 64115-88-4, 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. 64115-88-4 name is 1-Bromo-2-(trifluoromethoxy)benzene, 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.

Synthesis of (2-amino-5-bromo-pyridin-3-yl)-(2-trifluoromethoxy-phenyl)-methanone To a flame-dried 100 ml round bottomed flask was added 1-bromo-2-(trifluoromethoxy)benzene (2.39 g, 9.9 mmol). The flask was fitted with a rubber septum, purged with nitrogen then charged with anhydrous THF (20 ml). The solution was cooled to -78 C. for 10 min, then a 2.5 M solution of n-butyl lithium in hexanes (3.9 ml, 9.8 mmol) was added dropwise over 3 minutes. The resulting solution was stirred at -78 C. for 40 minutes under nitrogen, then a solution of 739 mg (2.84 mmol) of 2-amino-5-bromo-N-methoxy-N-methyl-nicotinamide in 5 ml of THF was added dropwise over 3 minutes. The resulting red solution was allowed to warm to room temperature over 5 hours, then the reaction was quenched by addition of 10 ml of a saturated aqueous solution of ammonium chloride. Ethyl acetate (50 ml) was added, and the layers were separated. The aqueous fraction was extracted three times with ethyl acetate, and the combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes gave 530 mg (52%) of (2-amino-5-bromo-pyridin-3-yl)-(2-trifluoromethoxy-phenyl)-methanone as a yellow-orange solid. 1H-NMR (CDCl3) delta=8.29 (d, 1H), 7.60 (m, 2H,), 7.45 (t, 1H), 7.42 (m, 3H), 1.79(br. s, 2H); MS m/z: 361 [MH]+.

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

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2006/30583; (2006); A1;,
Ether – Wikipedia,
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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. 1758-46-9, name is 2-Phenoxyethylamine, A new synthetic method of this compound is introduced below., Computed Properties of C8H11NO

General procedure: A solution of 2-phenoxyethylamine (1.31 mL, 10 mmol) in methanol (10 mL) was added to a solution of triethylamine(Et3N) (2.76 mL, 20 mmol) in methanol (10 mL) at 0 C. A solution of 2-chloropyridine (3.80 mL, 40 mmol) in methanol(10 mL) was then added at 0 C under N2. After being stirred for 30 min, the reaction mixture was heated to 25 C and stirred for 3 days. Then, the solvent was evaporated under reduced pressure to afford a yellow solid L1 washed with methanol and dried under vacuum. Yield: 2.31 g (79%).FTIR data (KBr, pellet, cm-1): upsilon 3335, 3057, 2922, 1573,1436, 1243. 1H NMR (400 MHz, CDCl3,ppm): delta 3.94 (t,2H, CH2,J 47.8 Hz), 4.59 (t, 2H, CH2),6.85 (t, 2H, Py-H),6.87 (d, 2H, Py-H, J 7.1 Hz), 7.15 (d, 2H, Ph-H), 7.26 (t,1H, Ph-H), 7.54 (t, 2H, Ph-H), 7.57 (t, 2H, Py-H), 8.33 (d,2H, Py-H). 13C NMR (100 MHz, CDCl3,ppm): delta 42.83,67.63, 115.72, 116.79, 117.17, 121.13, 130.02, 137.32,147.14, 157.30, 159.39. ESI-MS (m/z): 291.16 [L1 + H]+.Anal. Calcd for C18H17N3O(Found) %: C, 74.23 (74.01); H,5.84 (5.71); N, 14.43 (14.13).

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:
Article; Wang, Jun; Liu, Jinyi; Chen, Liduo; Lan, Tianyu; Wang, Libo; Transition Metal Chemistry; vol. 44; 7; (2019); p. 681 – 688;,
Ether – Wikipedia,
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