59786-31-1 | Pyridine-derivatives

Extended knowledge of Methyl 3-bromoisonicotinate

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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. 59786-31-1, name is Methyl 3-bromoisonicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-bromoisonicotinate

Example 55 Synthesis of (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-3-(5-methylfuran-2-yl)isonicotinamide Compound 106a. To a stirred solution methyl 3-bromoisonicotinate (0.300 g, 1.4 mmol, 1.0 equiv) in Dioxan (5 mL) and water (5 mL), was added (5-methylfuran-2-yl)boronic acid (0.212 g, 1.68 mmol, 1.2 equiv), Na2CO3 (0.297 g, 2.8 mmol, 2.0 equiv) and aerated the reaction mixture with nitrogen for 15 min and added Dichlorobis(triphenylphosphine)palladium(II) (0.098 g, 0.14 mmol, 0.1 equiv). Aerated the reaction mixture again with nitrogen for 15 min. The mixture was allowed to stir at 100 C. for 2 h. Product formation was confirmed by LCMS. The reaction mixture was diluted with water (50 mL) and washed with ethyl acetate (20 mL*2). Aqueous layer was separated and freeze dried over lyophilizer to obtain 3-(5-methylfuran-2-yl)isonicotinic acid (0.250 g).

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Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

26-Sep News Some scientific research about 59786-31-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59786-31-1, Methyl 3-bromoisonicotinate, 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.59786-31-1, name is Methyl 3-bromoisonicotinate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.Computed Properties of C7H6BrNO2

Step A Preparation of 3-(4-cyanobenzyl)pyridin-4-carboxylic acid methyl ester A solution of 4-cyanobenzyl bromide (625 mg, 3.27 mmol) in dry THF (4 mL) was added slowly over ~3 min. to a suspension of activated Zn (dust; 250 mg) in dry THF (2 mL) at 0° under an argon atmosphere. The ice-bath was removed and the slurry was stirred at room temperature for a further 30 min. Then 3-bromopyridin-4-carboxylic acid methyl ester (540 mg. 2.5 mmol) followed by dichlorobis(triphenylphosphine)nickel (II) (50 mg). The resultant reddish-brown mixture was stirred for 3 h at ~40°-45° C. The mixture was cooled and distributed between EtOAc (100 ml,) and 5percent aqueous citric acid (50 mL). The organic layer was washed with H2 O(2*50 mL), dried with Na2 SO4. After evaporation of the solvent the residue was purified on silica gel, eluding with 35percent EtOAc in hexane to give 420 mg as a clear gum. FAB ms (M+1)253.

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Reference:
Patent; Merck & Co., Inc.; US5859012; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

26-Sep News Some scientific research about 59786-31-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59786-31-1, Methyl 3-bromoisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5859012; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some scientific research about 59786-31-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59786-31-1, Methyl 3-bromoisonicotinate, and friends who are interested can also refer to it.

Related Products of 59786-31-1, 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. 59786-31-1, name is Methyl 3-bromoisonicotinate. A new synthetic method of this compound is introduced below.

Example 68 Synthesis of (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-3-(piperidin-4-ylamino)isonicotinamide Compound 118a. To a stirred solution of methyl 3-bromoisonicotinate (0.500 gm, 2.3148 mmol, 1 equiv) & tert-butyl 4-aminopiperidine-1-carboxylate (0.463 gm, 2.3148 mmol, 1 equiv) and CS2CO3 (1.5 gm, 4.6296 mmol, 2 equiv) in dioxane (15 mL). The resulting mixture was purged with nitrogen for 10 min followed by addition of Pd2(dba)3 (0.106 gm, 0.1157 mmol, 0.05 equiv) and xantphos (0.134 gm, 0.2314 mmol, 0.1 equiv), again purged with nitrogen for 10 min. The reaction mixture was heated at 120 C. for overnight. The progress of reaction was monitored by LCMS. The reaction mixture was diluted with water (30 mL), extracted with EtOAc (2*50 mL). The combined organic layers were washed with water (30 mL), with brine (30 mL), dried over Na2SO4, concentrated to afford the crude which was purified by flash chromatography to obtain methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinate (400 mg, 51.49%) as a white solid. LCMS: 336.3 [M+H]+ 1H NMR: (400 MHz, DMSO-d6) delta 8.41 (s, 1H), 7.60-7.51 (m, 2H), 7.27 (d, J=7.9 Hz, 1H), 3.00 (m., 4H), 2.04-1.88 (s, 3H), 1.44-1.35 (s, 9H), 1.31-1.12 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59786-31-1, Methyl 3-bromoisonicotinate, and friends who are interested can also refer to it.

Brief introduction of Methyl 3-bromoisonicotinate

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. 59786-31-1, Methyl 3-bromoisonicotinate, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 59786-31-1 ,Some common heterocyclic compound, 59786-31-1, molecular formula is C7H6BrNO2, 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.

PdCl2(PPh3)2 (0.7 g, 1.03 mmol, 0.05 eq.) was added to a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (6.3 g, 20.5 mmol, 1.0 eq.) in THF (120 mL) under nitrogen. To this was added 3-bromoisonicotinic acid methyl ester (4.4 g, 20.5 mmol, 1.0 eq.). This was followed by the addition of a solution of Na2CO3 (8.7 g, 82.1 mmol, 4.0 eq.) in water (41 mL). The resulting solution was stirred for 14 hours while the temperature was maintained at reflux in an oil bath. The resulting solution was diluted with EtOAc (100 mL), and washed with saturated aqueous NaCl (2*100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:10) to yield 3′,6′-dihydro-2’H-[3,4′]bipyridinyl-4,1′-dicarboxylic acid 1′-t-butyl ester 4-methyl ester (5.6 g) as a yellow oil. H-NMR: (300 MHz, CDCl3, ppm): 8.65 (1H, d, J=4.8 Hz), 8.54 (1H, s), 7.65 (1H, d, J=4.8 Hz), 5.65 (1H, m), 4.08 (2H, m), 3.90 (3H, s), 3.65 (2H, m), 2.34 (2H, m), 1.51 (9H, s).

Reference:
Patent; Stangeland, Eric L.; Patterson, Lori Jean; Zipfel, Sheila; US2011/230495; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new synthetic route of 59786-31-1

Reference of 59786-31-1 ,Some common heterocyclic compound, 59786-31-1, molecular formula is C7H6BrNO2, 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.

Compound 115a. To a solution of methyl 3-bromoisonicotinate (0.2 g, 0.93 mmol, 1.0 equiv) in Dioxane (10 mL) was added benzenethiol (0.204 g, 1.85 mmol, 2.0 equiv), KOAc (0.184 g, 1.876 mmol, 2.0 equiv) and resulting reaction mixture purged with N2 gas for 10 minute, followed by the addition of Pd2(dba)3 (0.042 g, 0.046 mmol. 0.05 equiv), Xanthphose (0.026 g, 0.046 mmol, 0.05 equiv) and resulting reaction mixture). The resulting reaction mixture was heated at 90 C. for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the mixture was filtered through celite bed, washed with ethyl acetate (100 mL). Filtrate was concentrated under reduced pressure. The crude product obtained was purified by flash chromatography (20% ethyl acetate hexane as an eluent) to obtain methyl 3-(phenylthio)isonicotinate (0.100 g, 44.4% Yield) as yellow oil. (0939) LCMS 246.1 [M+H]+ (0940) 1H NMR (400 MHz, DMSO-d6) delta 8.92 (br. s., 1H), 8.76-8.56 (m, 2H), 7.50 (s, 1H), 7.48-7.40 (m, 2H), 7.40-7.29 (m, 2H), 5.14-5.04 (m, 1H), 4.21 (br. s., 1H), 4.03 (d, J=2.6 Hz, 2H), 2.87 (br. s., 1H), 2.79 (d, J=14.5 Hz, 1H), 2.67 (br. s., 1H).

Some scientific research about Methyl 3-bromoisonicotinate

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 59786-31-1, Methyl 3-bromoisonicotinate.

Reference of 59786-31-1, 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. 59786-31-1, name is Methyl 3-bromoisonicotinate, molecular formula is C7H6BrNO2, The 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.

Compound 43a. To a solution of ethyl 3-bromoisonicotinate (0.4 g, 1.85 mmol, 1.0 equiv) in toluene (20 mL) was added 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.58 g, 2.77 mmol, 1.5 equiv), K2CO3 (0.51 g, 3.78 mmol, 2.0 equiv) and resulting reaction mixture purged with N2 gas for 10 min. followed by the addition of Pd(PPh3)4 (0.065 g, 0.093 mmol. 0.05 equiv). The resulting reaction mixture was heated at 100 C. for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the reaction mixture was filtered through Celite bed, washed with ethyl acetate (100 mL). Filtrate was concentrated under reduced pressure. The crude product obtained was purified by flash chromatography (0-10% ethyl acetate in hexane as an eluent) to obtain methyl 3-(cyclohex-1-en-1-yl)isonicotinate (0.170 g, 42.4%) as colorless oil. (0763) LCMS 218.2 [M+H]+ (0764) 1H NMR (400 MHz, DMSO-d6) delta 8.60 (d, J=5.3 Hz, 1H), 8.52 (s, 1H), 7.56 (d, J=5.3 Hz, 1H), 5.62 (br. s., 1H), 2.24-2.06 (m, 4H), 1.77-1.54 (m, 4H).