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Step A. Methyl 5 -bromo-3 -chloropicolinateTo a round bottle flask with <strong>[1189513-51-6]5-bromo-3-chloropicolinic acid</strong> (4.2 mmol, 1.0 g) in MeOH (10 mL)was added 50C12 (5.1 mmol, 0.37 mL) dropwise at RT. The reaction mixture was refluxed for1.5 h. After the solvent was removed, EtOAc was added to the residue, and the pH was adjusted to 7.0 by addition of sat. aq. NaHCO3. The organic layer was dried over Na2504, filtered, and concentrated in vacuo to give the title compound. MS (ESI) mlz = 250, 252 (M+H)
With thionyl chloride; at 20℃; for 1.5h;Reflux;
To a round bottle flask with <strong>[1189513-51-6]5-bromo-3-chloropicolinic acid</strong> (4.2 mmol, 1.0 g) in MeOH (10 mL) was added SOCl2 (5.1 mmol, 0.37 mL) dropwise at RT. The reaction mixture was refluxed for 1.5 h. After the solvent was removed, EtOAc was added to the residue, and the pH was adjusted to 7.0 by addition of sat aq. NaHC03. The organic layer was dried over Na2S04, filtered, and concentrated in vacuo to give the title compound. (1183) MS (ESI) m/z = 250, 252 (M+H)
55 g
To a slightly cloudy solution of <strong>[1189513-51-6]5-bromo-3-chloro-pyridine-2-carboxylic acid</strong> (60 g, 183.2 mmol) in dichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalyl chloride (24,9 ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at ambient temperature. Theresulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761.3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at ambient temperature. After neutralisation with an aqueous saturated solution of sodium hydrogen carbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5-bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method B): 250/252/254 (M+1), retention time 1.12 mm.
55 g
To a slightly cloudy solution of <strong>[1189513-51-6]5-bromo-3-chloro-pyridine-2-carboxylic acid</strong> (60 g, 183.2 mmol) indichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalylchloride (24,9ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at ambient temperature. The resulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761.3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at ambient temperature. After neutralisation with an aqueous saturated solution of sodium hydrogencarbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5-bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method 2): 250/252/254 (M+1), retention time 1.12 mm.
55 g
Step 1: Preparation of methyl 5-bromo-3-chloro-pyridine-2-carboxylate To a slightly cloudy solution of <strong>[1189513-51-6]5-bromo-3-chloro-pyridine-2-carboxylic acid</strong> (60 g, 183.2 mmol) in dichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalylchloride (24,9 ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at room temperature. The resulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761.3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at room temperature. After neutralisation with an aqueous saturated solution of sodium hydrogen carbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5-bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method 2): 250/252/254 (M+1)+ , retention time 1.12 min.
55 g
To a slightly cloudy solution of <strong>[1189513-51-6]5-bromo-3-chloro-pyridine-2-carboxylic acid</strong> (60 g, 183.2 mmol) in dichloromethane (700 ml) was added dropwise N,N-dimethylformamide (1 ml) and oxalylchloride (24,9 ml, 286.9 mmol). The cloudy solution was stirred for 3 hours at ambient temperature. The resulting yellow solution was cooled to 10°C and methanol (30.8 ml, 761 .3 mmol) was added dropwise to the mixture, keeping the temperature between 15° and 20°C. The solution was stirred overnight at ambient temperature. After neutralization with an aqueous saturated solution of sodium hydrogen carbonate, the organic layer was washed with brine, dried over sodium sulfate, filtrated and evaporated to give methyl 5- bromo-3-chloro-pyridine-2-carboxylate (55 g) as a yellow solid, which was used without further purification. LCMS (method 2): 250/252/254 (M+1 )+, retention time 1 .12 min.
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