Simple exploration of Methyl 3-chloroisonicotinate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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, Recommanded Product: 98273-79-1, blongs to pyridine-derivatives compound. Recommanded Product: 98273-79-1

A 2.5 M hexane solution of BuLi (16.79 mL, 42.0 mmol) was added dropwise to a solution of diisopropylamine (6.23 mL, 43.7 mmol) in THF (150 mL) at -78 0C. The mixture was stirred at 0 0C for 15 min and cooled to -78 0C. Acetonitrile (2.192 mL, 42.0 mmol) was added dropwise. The solution gradually turned to milky white. After 1 h at -78 0C, methyl 3-chloroisonicotinate (3.00 g, 17.48 mmol) in THF (10 mL) was added dropwise. The flask was rinsed with THF (2 mL) and added. After 1 h at -78 0C, the mixture was quenched with brine (200 mL) and acidified to pH~l. THF was evaporated in vacuo. The aqueous residue was extracted withEtOAc (3×100 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4) and concentrated to give impure 3-(3-chloropyridin-4-yl)-3- oxopropanenitrile as a tan solid (3.12 g, 81% pure, 80% yield). MS (ES+) m/z: 181 (M+H); LC retention time: 1.90 min (analytical HPLC Method A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/100171; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Simple exploration of Methyl 3-chloroisonicotinate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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, Recommanded Product: 98273-79-1, blongs to pyridine-derivatives compound. Recommanded Product: 98273-79-1

A 2.5 M hexane solution of BuLi (16.79 mL, 42.0 mmol) was added dropwise to a solution of diisopropylamine (6.23 mL, 43.7 mmol) in THF (150 mL) at -78 0C. The mixture was stirred at 0 0C for 15 min and cooled to -78 0C. Acetonitrile (2.192 mL, 42.0 mmol) was added dropwise. The solution gradually turned to milky white. After 1 h at -78 0C, methyl 3-chloroisonicotinate (3.00 g, 17.48 mmol) in THF (10 mL) was added dropwise. The flask was rinsed with THF (2 mL) and added. After 1 h at -78 0C, the mixture was quenched with brine (200 mL) and acidified to pH~l. THF was evaporated in vacuo. The aqueous residue was extracted withEtOAc (3×100 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4) and concentrated to give impure 3-(3-chloropyridin-4-yl)-3- oxopropanenitrile as a tan solid (3.12 g, 81% pure, 80% yield). MS (ES+) m/z: 181 (M+H); LC retention time: 1.90 min (analytical HPLC Method A).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/100171; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Extracurricular laboratory: Synthetic route of Methyl 3-chloroisonicotinate

The synthetic route of 98273-79-1 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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, COA of Formula: C7H6ClNO2, blongs to pyridine-derivatives compound. COA of Formula: C7H6ClNO2

To a solution of 3-chloro-pyridine-4-carboxylic acid methyl ester (0.28 g, 1.65 mmol) in DMF (10 ml) are added cesium carbonate (2.68 g, 8.25 mmol) and 3,3-difluoro-3-(4-fluorophenyl)-propane-1-thiol (synthesized according to the methods described in sections a) and b) of example 3) (0.34 g, 1.65 mmol) in a sealed tube. The reaction mixture is stirred at 90 C. for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% acetone/hexane) to yieldb3-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.19 g, 0.56 mmol, 34%).

The synthetic route of 98273-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; LUCAS, Simon; Kuehnert, Sven; Bahrenberg, Gregor; Schroeder, Wolfgang; US2014/148468; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New downstream synthetic route of Methyl 3-chloroisonicotinate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Quality Control of Methyl 3-chloroisonicotinate

A solution of 1-(bromomethyl)-4-(methylsulfanyl)benzene (prepared according to D. D. M. Wayner, D. R. Arnold, Can J. Chem., 1984, 62, 1164) (2.54 g, 11.7 mmol) in THF (10 mL) was added dropwise to a slurry of Riecke Zinc in THF (22.8 mL of a commercial suspension [5g Zn/100 mL], 17.5 mmol) under nitrogen. During this time the temperature rose steadily to 35C. After allowing the black slurry to cool to room temperature over 30 min bis(triphenylphosphine)nickel (II) chloride (762 mg, 1.17 mmol) was added followed by a solution of methyl 3-chloroisonicotinate (prepared according to J. Epsztajn, M. W. Plotka, A. Grabowska, Synth. Commun., 1997, 27, 1075) (1.0 g, 5.83 mmol) in THF (10 mL), dropwise, taking care to keep the temperature below 30C. After the addition was complete the reaction was allowed to cool to room temperature over 1 h before being quenched by the addition of sat. NH4Cl (aq) (20 mL) while cooling with an ice bath. The mixture was filtered through Celite ), washing well with EtOAc (3 x 20 mL), the organic layer was separated, dried (MgS04) and evaporated to give a brown oil. The residue was purified by column chromatography [SiO2; EtOAc:pentane, 1:3 increasing polarity to EtOAc:pentane, 1:1 and then to (EtOAc:MeOH:NH40H, 95:5:0.5):pentane, 1:1] to give the title compound as an orange oil; & delta H (CDCl3, 400 MHz) 2.43 (3H, s), 3.82 (3H, s), 4.30 (2H, s), 7.05 (2H, d), 7.18 (2H, d), 7.67 (1H, br), 8.59 (2H, br); MS m/z (TS+) 274 (MH+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Limited; Pfizer Inc.; WO2004/16593; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Simple exploration of Methyl 3-chloroisonicotinate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Product Details of 98273-79-1

INTERMEDIATE 22Methyl 3-(3′-ethoxy-3-fluorobiphenyl-4-ylamino)isonicotinate; A mixture of methyl 3-chloroisonicotinate (1.00 g, 5.83 mmol), intermediate 1 (1.35 g, 5.83 mmol), Cs2CO3(2.66 g, 8.16 mmol) and Xantphos (0.68 g, 1.17 mmol) in dioxane (20 mL) was stirred under argon atmosphere for 10 min. Then Pd2(dba)3 (0.53 g, 0.58 mmol) was added and the mixture stirred under argon atmosphere at 12O0C overnight. The reaction mixture was filtered over Celite and washed with CH2CI2. The filtrate was concentrated and purified by column chromatography eluting with EtOAc/hexane/Et3N (20/79/1) and the desired compound was obtained. Yield=51% LRMS: m/z 367 (M+1 )+.1H NMR (250 MHz1 CDCI3) delta ppm: 9.26 (s, 1 H); 8.8 (s, 1H); 8.25 (d, J = 5.3 Hz, 1 H); 7.87 (d, J = 5.3 Hz, 1 H); 7.72-7.45 (m, 4H); 7.3 (d, J = 8.2 Hz, 1 H); 7.26 (s, 1H); 7.05 (dd, J = 8.2, J= 1.8 Hz, 1 H); 4.25 (c, J = 7 Hz, 2H); 4.12 (s, 3H); 1.61 (t, J = 7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2008/77639; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Simple exploration of Methyl 3-chloroisonicotinate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.98273-79-1, name is Methyl 3-chloroisonicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Product Details of 98273-79-1

INTERMEDIATE 22Methyl 3-(3′-ethoxy-3-fluorobiphenyl-4-ylamino)isonicotinate; A mixture of methyl 3-chloroisonicotinate (1.00 g, 5.83 mmol), intermediate 1 (1.35 g, 5.83 mmol), Cs2CO3(2.66 g, 8.16 mmol) and Xantphos (0.68 g, 1.17 mmol) in dioxane (20 mL) was stirred under argon atmosphere for 10 min. Then Pd2(dba)3 (0.53 g, 0.58 mmol) was added and the mixture stirred under argon atmosphere at 12O0C overnight. The reaction mixture was filtered over Celite and washed with CH2CI2. The filtrate was concentrated and purified by column chromatography eluting with EtOAc/hexane/Et3N (20/79/1) and the desired compound was obtained. Yield=51% LRMS: m/z 367 (M+1 )+.1H NMR (250 MHz1 CDCI3) delta ppm: 9.26 (s, 1 H); 8.8 (s, 1H); 8.25 (d, J = 5.3 Hz, 1 H); 7.87 (d, J = 5.3 Hz, 1 H); 7.72-7.45 (m, 4H); 7.3 (d, J = 8.2 Hz, 1 H); 7.26 (s, 1H); 7.05 (dd, J = 8.2, J= 1.8 Hz, 1 H); 4.25 (c, J = 7 Hz, 2H); 4.12 (s, 3H); 1.61 (t, J = 7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2008/77639; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Share a compound : Methyl 3-chloroisonicotinate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 98273-79-1, Methyl 3-chloroisonicotinate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of 3-chloro-pyridine-4-carboxylic acid methyl ester (0.28 g, 1.65 mmol) in DMF (10 ml) are added cesium carbonate (2.68 g, 8.25 mmol) and 3,3-difluoro-3-(4-fluorophenyl)-propane-1 -thiol (synthesized according to the methods described in sections a) and b) of example 3) (0.34 g, 1.65 mmol) in a sealed tube. The reaction mixture is stirred at 90C for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3 x 20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% acetone/hexane) to yield 3-[[3,3- difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.19 g, 0.56 mmol, 34%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98273-79-1, Methyl 3-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; GRUNENTHAL GMBH; LUCAS, Simon; KUeHNERT, Sven; BAHRENBERG, Gregor; SCHROeDER, Wolfgang; WO2014/82737; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem