Category: 437-83-2

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. 437-83-2, name is 3-Fluoro-2-methoxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Fluoro-2-methoxyaniline

General procedure: NaNO2 (12.0 g, 173 mmol, in 40 mL of water) solution was addeddropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 mL of hydrobromic acid (47 %) and100 mL of water at -5 ~ 0 C and stirred for 1 hour. This solution was then added slowly to the suspension of CuBr(45.2 g, 315 mmol) in 50 mL of hydrobromic acid (47 %) at 0 C. The resulting mixture was stirred at 0 C for 1 hourthen warmed to 50 C and stirred for 1 hour. The reaction mixture was poured into ice water and extracted withether (2 X 500 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentratedto give 1-bromo-3-fluoro-2-methoxybenzene.

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; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 437-83-2, A common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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[00180j To a stirred solution of Intermediate 1(0.33 g, 1.61 mmol) in DMA (3 mL) was added 3-fluoro-2-methoxyaniline (0.27 g, 1.9 mmol) followed by NaHMDS (1M in THF, 4.83mL, 4.83 mmol). The reaction was stirred for 30 minutes and then water (30 mL) was gradually added resulting in the product crashing out as a precipitate. The product was collected by filtration, washed with additional water and then dried undervacuum providing Intermediate 15 (476 mg, 95% yield). LC retention time 3.22 mm [A]. MS(Ej m/z: 310 (MHj.

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; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; LIN, Shuqun; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; WO2014/74660; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 437-83-2, name is 3-Fluoro-2-methoxyaniline, 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 437-83-2, name: 3-Fluoro-2-methoxyaniline

Example 91 8-Ethyl-2-(3-fluoro-2-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one A mixture of 8-ethyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (133 mg, 0.56 mmol) and 500 muL of 3-fluoro-2-methoxyaniline was heated at 175 C. for 20 minutes. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluding with ethyl acetate. Recrystallization from ethyl acetate and hexane provided 28 mg (16%) of 8-ethyl 2-(3-fluoro-2-methoxyplhenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one, mp 92-93 C. Analysis calculated for C16H15N4O2F 0.15 H2O: C, 60.63; H, 4.83; N, 17.68. Found: C, 60.31; H, 4.52; N, 17.42.

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-Fluoro-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Booth, Richard John; Chatterjee, Arindam; Malone, Thomas Charles; US2004/224958; (2004); 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

Application of 437-83-2, A common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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[00180j To a stirred solution of Intermediate 1(0.33 g, 1.61 mmol) in DMA (3 mL) was added 3-fluoro-2-methoxyaniline (0.27 g, 1.9 mmol) followed by NaHMDS (1M in THF, 4.83mL, 4.83 mmol). The reaction was stirred for 30 minutes and then water (30 mL) was gradually added resulting in the product crashing out as a precipitate. The product was collected by filtration, washed with additional water and then dried undervacuum providing Intermediate 15 (476 mg, 95% yield). LC retention time 3.22 mm [A]. MS(Ej m/z: 310 (MHj.

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; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; LIN, Shuqun; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; WO2014/74660; (2014); 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. 437-83-2, name is 3-Fluoro-2-methoxyaniline, A new synthetic method of this compound is introduced below., SDS of cas: 437-83-2

General procedure: NaNO2 (12.0 g, 173 mmol, in 40 mL of water) solution was addeddropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 mL of hydrobromic acid (47 %) and100 mL of water at -5 ~ 0 C and stirred for 1 hour. This solution was then added slowly to the suspension of CuBr(45.2 g, 315 mmol) in 50 mL of hydrobromic acid (47 %) at 0 C. The resulting mixture was stirred at 0 C for 1 hourthen warmed to 50 C and stirred for 1 hour. The reaction mixture was poured into ice water and extracted withether (2 X 500 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentratedto give 1-bromo-3-fluoro-2-methoxybenzene.

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; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 437-83-2, 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 437-83-2 as follows.

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 (7.4Og, 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 l-bromo-3-fluoro- 2-methoxybenzene as a brown oil. This product is of sufficient purity (>95% by NMR spectroscopy) to use directly in the next synthetic step. 1H NMR (CDCl3): 53.95 (d, JH-F = 1.5 Hz, 3H, OCH3), 6.88 (apparent t of d, JH_H = 8.0 Hz, JH-F = 5.5 Hz, IH, H-5), 7.04 (d, JH-F = 10.5 Hz, JH-H = 8.0 Hz, JH-H = 1.5 Hz,~lH, H-4), 7.30 (d of apparent t, JH_H = 8.0 Hz, JH-H = 1.5 EPO Hz, JH-F = 1.5 Hz, IH5 H-6). 19F(1H) NMR (CDCl3): 5-127.7 (s). 13C(1H) NMR (CDCl3): delta 61.4 (d, JC_F = 5.0 Hz, OCH3), 116.2 (d, JC_F = 19.5 Hz5 C-4), 117.7 (d, JC-F = 3.0 Hz5 C-I)5 124.5 (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 Hz5 C-2), 156.2 (d, Jc-F = 250.5 Hz5 C-3).

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

Synthetic Route of 437-83-2, 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 437-83-2 as follows.

A mixture of (3-fluoro-2-methoxyphenyl)amine (5 g, 35.4 mmol) and 2,6-lutidine (7.4 mL, 64 mmol) in dichloromethane (20 mL) was treated at O0C dropwise with a solution of cinnamoylchloride (7.08 g, 42.5 mmol) in dichloromethane (30 mL). The reaction mixture was allowed to reach room temperature and was stirred over night. It was quenched with potassium phosphate buffer (50 mL, IM, pH 7) and stirred for 15 minutes. Dichloromethane was removed under reduced pressure and it was extracted with ethyl acetate. The organic phase was washed with phosphate buffer (like above, 100 mL), dried over sodium sulfate and concentrated to dryness. The residue was crystallized from ethyl acetate/ hexanes and then recrystallized from hexanes to give the product as colorless solid (6.21 g, 65%), mp 8O0C. MS (ESP^; 272 (MH+) for C16H14FNO21H-NMR (DMSO-AO delta: 3.88 (s, 3H); 6.97-7.12 (m, 2H); 7.23 (d, IH); 7.38-7.48 (m, 3H); 7.56-7.65 (m, 3H); 8.05 (m, IH); 9.61 (s, IH).

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

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 437-83-2 as follows. name: 3-Fluoro-2-methoxyaniline

A mixture of 3-fluoro-2-methoxyaniline (1.0 g, 7.1 mmol) and K2CO3 (1.04 g, 7.8 mmol) in DMF (15 mL) was added 1-bromobut-2-yne (981 mg, 7.1 mmol) was stirred at r.t. overnight. The resulting mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-20% EtOAc in PE) to afford the title compound (552 mg, 40% yield) as a yellow oil. LC-MS (ESI): m/z (M+1) = 193.91.

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIIV HEALTHCARE UK LIMITED; JOHNS, Brian Alvin; VELTHUISEN, Emile Johann; WEATHERHEAD, Jason Gordon; (225 pag.)WO2017/93938; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 437-83-2, 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 437-83-2 as follows.

Compound 123: 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-2-fluoro-3-methoxybenzoic acid; [0590] 4-Bromo-3-fluoro-2-methoxyaniline: To 3-fluoro-2-methoxyaniline (2.8 g, 20 mmol) in 10 mL of acetic acid was added bromine (0.82 mL, 16 mmol) in acetic acid (10 rnL) dropwise. The reaction mixture was stirred at rt. for 30 min. Solid was filtered and washed with acetic acid to give the HBr salt. It was then dissolved in water, basified by addition of KOH, extracted with ethyl acetate. The organic layer was dried and concentrated to give a white solid (2.8 g, 80 %). 1U NMR (400 MHz, CHLOROFORM-J) delta ppm 3.93 (s, 3 H) 6.42 (dd, J=S.6, 1.8 Hz, 1 H) 7.01 (dd, J=8.6, 7.1 Hz, 1 H). [M+H] calc’d for C7H7BrFNO, 222; found 222.

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/42711; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem