Category: 156094-63-2

Electric Literature of 156094-63-2 , The common heterocyclic compound, 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine, molecular formula is C7H8BrNO, 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.

General procedure: To a flame-dried flask containing z-BuOK (1.10 equiv.) and anhydrous DMF (2.5 mL/mmol) was added ethyl 2-((diphenylmethylene)amino)acetate (1.05 eq. ) at 0 C under argon. After 10 min, arylmethyl bromide (1.0 eq.) was added. The resulting reaction mixture was stirred at 0 C for 10 min and was allowed to warm up to 4 C and stirred at 4 C overnight. The reaction mixture was then slowly poured into water, extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure to evaporate the DCM solvent. The residue was then treated with a mixture of EtOH/concentrated HC1 (25:1 v/v). The resulting solution was stirred at room temperature for 2 h. Upon the evaporation of EtOH and most of the DMF, the residue was basified by 2 N K2CO3 solution to pH > 10 and extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure. The residue was purified through flash chromatography on silica gel (1: 19 CH3OH/CH2CI2) to afford the desired ethyl 2-amino-3- arylpropanoate product as a colorless gel.

The synthetic route of 156094-63-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DE BRABANDER, Jef; ROSENBAUM, Daniel; LIANG, Qiren; WANG, Wentian; (343 pag.)WO2019/191327; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156094-63-2 , The common heterocyclic compound, 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine, molecular formula is C7H8BrNO, 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.

General procedure: To a flame-dried flask containing z-BuOK (1.10 equiv.) and anhydrous DMF (2.5 mL/mmol) was added ethyl 2-((diphenylmethylene)amino)acetate (1.05 eq. ) at 0 C under argon. After 10 min, arylmethyl bromide (1.0 eq.) was added. The resulting reaction mixture was stirred at 0 C for 10 min and was allowed to warm up to 4 C and stirred at 4 C overnight. The reaction mixture was then slowly poured into water, extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure to evaporate the DCM solvent. The residue was then treated with a mixture of EtOH/concentrated HC1 (25:1 v/v). The resulting solution was stirred at room temperature for 2 h. Upon the evaporation of EtOH and most of the DMF, the residue was basified by 2 N K2CO3 solution to pH > 10 and extracted with DCM. The combined organic layers were dried over Na SCfl, filtered and concentrated under reduced pressure. The residue was purified through flash chromatography on silica gel (1: 19 CH3OH/CH2CI2) to afford the desired ethyl 2-amino-3- arylpropanoate product as a colorless gel.

The synthetic route of 156094-63-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DE BRABANDER, Jef; ROSENBAUM, Daniel; LIANG, Qiren; WANG, Wentian; (343 pag.)WO2019/191327; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, name: 2-(Bromomethyl)-6-methoxypyridine, blongs to pyridine-derivatives compound. name: 2-(Bromomethyl)-6-methoxypyridine

Substitution of 2-bromomethyl-6-methoxypyridine for 2-chloromethyl-3-methoxypyridine in the general procedure of Example 1(iii)-(v) leads to the preparation of N-cyano-N’-methyl-N”-[2-((6-methoxy-2-pyridyl)methylthio)ethyl]guanidine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4083983; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, SDS of cas: 156094-63-2, blongs to pyridine-derivatives compound. SDS of cas: 156094-63-2

To 3-iodo-4-nitro-lH-indazole (5.01 g, 17.3 mmol) in DMF (40 mL) was added K2CO3 (4.79 g, 34.7 mmol) and 2-(bromomethyl)-6-methoxypyridine (4.20 g, 20.8 mmol). The reaction mixture was stirred for 4 hours. The reaction mixture was concentrated to remove DMF, diluted with EtOAc and washed with H20 and brine. The organic phase was dried (Na2S04) and concentrated. Silica gel chromatography (EtOAc/Hexane 1 :5) gave the desired product (5.68 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BRADLEY, Michael; DELISLE, Robert Kirk; HENNINGS, D. David; KENNEDY, April L.; MARMSATER, Fredrik P.; MEDINA, Matthew; MUNSON, Mark C.; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2011/79076; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 156094-63-2, Adding some certain compound to certain chemical reactions, such as: 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine,molecular formula is C7H8BrNO, 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 156094-63-2.

[00602] A 60 % dispersion of sodium hydride in mineral oil (0.019 g, 0.493 mmol) was added to a stirred solution of 2-(phenoxymethyl)-6,7-dihydropyrazolo[l,5-a]pyrazin- 4(5H)-one (0.1 g, 0.411 mmol) in DMF (4 mL) at 0 C. The mixture was stirred at room temperature for 15 min. Then 2-bromomethyl-6-methoxypyridine (0.99 g, 0.493 mmol) was added and the mixture was stirred at room temperature for 16 h. The mixture was cooled at 0 C, treated with water and extracted with AcOEt. The organic layer was separated, washed with brine, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash chromatography (silica; EtOAc in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to afford an impure product that was repurified by flash column chromatography (silica; DCM). The desired fractions were collected and the solvents evaporated in vacuo. The desired product was triturated with diethyl ether and filtered to yield 5-[(6-methoxypyridin-2-yl)methyl]-2-(phenoxymethyl)-6,7- dihydropyrazolo[l,5-a]pyrazin-4(5H)-one (0.105 g, 70.5% yield). C2oH2oN403 *H NMR (400 MHz, CDC13) delta ppm 3.87 (s, 3 H) 3.90 – 3.98 (m, 2 H) 4.37 – 4.44 (m, 2 H) 4.76 (s, 2 H) 5.09 (s, 2 H) 6.65 (d, J=8.1 Hz, 1 H) 6.90 (d, J=7.2 Hz, 1 H) 6.93 – 7.04 (m, 4 H) 7.26 – 7.33 (m, 2 H) 7.54 (dd, J=8.2, 7.3 Hz, 1 H).

According to the analysis of related databases, 156094-63-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P., Jeffrey; LINDSLEY, Craig, W.; STAUFFER, Shaun, R.; BARTOLOME-NEBREDA, Jose Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; TONG, Han Min; ALCAZAR-VACA, Manuel Jesus; ANDRES-GIL, Jose Ignacio; WO2013/192350; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, Safety of 2-(Bromomethyl)-6-methoxypyridine, blongs to pyridine-derivatives compound. Safety of 2-(Bromomethyl)-6-methoxypyridine

A room temperature solution of 4-(6-(piperazin- 1 -yl)pyridin-3 -yl)-6-( 1 H-pyrazol-4- yl)pyrazolo[1,5-a]pyridine-3-carbonitrile bis(2,2,2-trifluoroacetate) (Example 698, Step 1; 6 mg, 0.0162 mmol) in dry DMA (900 tL) was treated sequentially with TEA (22.6 tL, 0.162 mmol) and 2-(bromomethyl)-6-methoxypyridine (9.82 mg, 0.0486 mmol). The reaction mixture was stirred overnight at room temperature before introducing additional TEA (1 tL, 0.01 mmol) and 2-(bromomethyl)-6-methoxypyridine (2mg, 0.01 mmol). The reaction mixture was stirred at room temperature until LCMS indicated the reaction was complete. The reaction mixture was directly purified by Cl 8 reverse-phase chromatography (15-80% ACN/water with 0.1% formic acid as the gradient eluent) to cleanly afford the title compound (2.5 mg, 51% yield). MS (apci) m/z = 492.2(M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, Safety of 2-(Bromomethyl)-6-methoxypyridine, blongs to pyridine-derivatives compound. Safety of 2-(Bromomethyl)-6-methoxypyridine

A room temperature solution of 4-(6-(piperazin- 1 -yl)pyridin-3 -yl)-6-( 1 H-pyrazol-4- yl)pyrazolo[1,5-a]pyridine-3-carbonitrile bis(2,2,2-trifluoroacetate) (Example 698, Step 1; 6 mg, 0.0162 mmol) in dry DMA (900 tL) was treated sequentially with TEA (22.6 tL, 0.162 mmol) and 2-(bromomethyl)-6-methoxypyridine (9.82 mg, 0.0486 mmol). The reaction mixture was stirred overnight at room temperature before introducing additional TEA (1 tL, 0.01 mmol) and 2-(bromomethyl)-6-methoxypyridine (2mg, 0.01 mmol). The reaction mixture was stirred at room temperature until LCMS indicated the reaction was complete. The reaction mixture was directly purified by Cl 8 reverse-phase chromatography (15-80% ACN/water with 0.1% formic acid as the gradient eluent) to cleanly afford the title compound (2.5 mg, 51% yield). MS (apci) m/z = 492.2(M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, 156094-63-2, blongs to pyridine-derivatives compound. name: 2-(Bromomethyl)-6-methoxypyridine

1.66 g (6.31 mmol) of triphenylphosphine and 685 mg (3.39 mmol) of 2-bromomethyl-6-methoxypyridine were mixed in 10 mL of benzene and heated up to 70 C under nitrogen atmosphere. The mixture was stirred in 25 hours, then cooled to ambient temperature. Theprecipitate was filtered and washed by 10 mL of benzene to give 1.47 g (3.17 mmol, 94 % yield) as awhite powder. The crude was used in the next reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156094-63-2, its application will become more common.

Reference:
Article; Kurihara, Seiya; Nishimura, Yoshinobu; Arai, Tatsuo; Bulletin of the Chemical Society of Japan; vol. 88; 7; (2015); p. 963 – 965;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, 156094-63-2, blongs to pyridine-derivatives compound. name: 2-(Bromomethyl)-6-methoxypyridine

1.66 g (6.31 mmol) of triphenylphosphine and 685 mg (3.39 mmol) of 2-bromomethyl-6-methoxypyridine were mixed in 10 mL of benzene and heated up to 70 C under nitrogen atmosphere. The mixture was stirred in 25 hours, then cooled to ambient temperature. Theprecipitate was filtered and washed by 10 mL of benzene to give 1.47 g (3.17 mmol, 94 % yield) as awhite powder. The crude was used in the next reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156094-63-2, its application will become more common.

Reference:
Article; Kurihara, Seiya; Nishimura, Yoshinobu; Arai, Tatsuo; Bulletin of the Chemical Society of Japan; vol. 88; 7; (2015); p. 963 – 965;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, 156094-63-2, blongs to pyridine-derivatives compound. name: 2-(Bromomethyl)-6-methoxypyridine

1.66 g (6.31 mmol) of triphenylphosphine and 685 mg (3.39 mmol) of 2-bromomethyl-6-methoxypyridine were mixed in 10 mL of benzene and heated up to 70 C under nitrogen atmosphere. The mixture was stirred in 25 hours, then cooled to ambient temperature. Theprecipitate was filtered and washed by 10 mL of benzene to give 1.47 g (3.17 mmol, 94 % yield) as awhite powder. The crude was used in the next reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156094-63-2, its application will become more common.

Reference:
Article; Kurihara, Seiya; Nishimura, Yoshinobu; Arai, Tatsuo; Bulletin of the Chemical Society of Japan; vol. 88; 7; (2015); p. 963 – 965;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem