Methyl 6-amino-3-bromopicolinate

d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHClTo a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHC1d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHCld) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl esterTo a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHC1Reference Example 17; methyl 6-amino-3-bromopyridine-2-carboxylate [Show Image]; To a suspension of methyl 6-aminopyridine-2-carboxylate (5.98 g, 39.5 mmol) and sodium carbonate (2.64 g, 24.9 mmol) in acetic acid (150 mL) was added bromine (7.89 g, 49.4 mmol), and the mixture was stirred at room temperature for 7 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. This was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70-->80/20) to give the title compound (2.67 g, yield 29percent). To a 100 mL round bottom flask, were added methyl 6-aminopicolinate (6 g, 0.0394 mol), sodium carbonate (2.64 g, 0.0248 mol) and acetic acid (300 mL). The reaction mixture was cooled to 0 - 5 °C. To the same flask, bromine (2 mL, 0.039 mol) was slowly added. The reaction mixture was stirred at room temperature for 5 h. The volatiles were evaporated under reduced pressure to get the residue. The residue was neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60 - 120 silica gel and 30 percent ethyl acetate in hexane to get the title compound [1 g, 11 percent]. b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (Si0b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (SiOTo a solution of

Molecular Weight:231.05
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:229.96909
Monoisotopic Mass:229.96909
Topological Polar Surface Area:65.2
Heavy Atom Count:12
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes