2-Pyridinecarboxylic acid, 3-amino-6-bromo-, methyl ester

(Step 2) (1071) To a mixture of methyl 3-aminopyridine-2-carboxylate (17 g, 111.8 mmol) in a mixed solvent of water (288 mL) and 2M sulfuric acid (58 mL) was added a solution of bromine (5.76 mL, 111.8 mmol) in acetic acid (43 mL) at room temperature, and the mixture was stirred at room temperature for 4 hr. The pH of the mixture was adjusted to 6 with 2N aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate (x2), the organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; dichloromethane) to give methyl 3-amino-6-bromopyridine-2-carboxylate (19.2 g, 74percent) as a white solid. Step 2;. Preparation of 3-amino-6-bromo-pyridine-2-carboxylic acid methyl ester; Add a solution of 2 M sulfuric acid (2 mL) to a suspension of 3-amino-pyridine-2- carboxylic acid methyl ester (0.59 g, 3.88 mmol) in water (10 mL) and stir the mixture until the precipitate is dissolved. Add dropwise a solution of bromine (0.199 mL, 3.88 mmol) in acetic acid (1.5 mL). Add a solution of 2 M sodium hydroxide until pH = 6 and extract with ethyl acetate. Separate the organic layer and extract with ethyl acetate. Dry the combined organic layers over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue using silica gel chromatography eluting with ethyl acetate/hexanes to afford the title compound (0.616 g, 69percent). H-NMR (CDCl3, 300 MHz) : No. 3.90 (s, 3 H) ; 6.90 (d, J = 8.5 Hz, 1H), 7.30 (d, J= 8.5 Hz, 1H).A solution of methyl 3-aminopyridine-2-carboxylate (1 g, 6.57 mmol, 1.00 equiv) and N-bromosuccinimide (1.29 g, 7.25 mmol, 1.10 equiv) in acetonitrile (25 mL) was stirred at room temperature. A solution of methyl 3-aminopyridine-2-carboxylate (1 g, 6.57 mmol, 1.00 equiv) andN-bromosuccinimide (1.29 g, 7.25 mmol, 1.10 equiv) in acetonitrile (25 mL) was stirred at room temperature. After being stirred for 2 h the mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to give the title compound (0.81 g, 54percent) as a yellow solid. LC-MS (ES, mlz): 231, 233 [M+H].4.1

Molecular Weight:231.05
XLogP3:1.9
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