5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester

To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (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.To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (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.Step 1: Preparation of methyl 5-bromo-3-chloro-pyridine-2-carboxylate To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (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.To a slightly cloudy solution of 5-bromo-3-chloro-pyridine-2-carboxylic acid (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 )

Molecular Weight:250.48
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:248.91922
Monoisotopic Mass:248.91922
Topological Polar Surface Area:39.2
Heavy Atom Count:12
Complexity:179
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes