5-Bromo-3-methoxy-2-pyridinecarbonitrile

5-bromo-3-methoxypicolinonitrile Sodium methoxide (9.7 g, 0.18 mol) in methanol (50 ml) was added dropwise to a suspension of 5-bromo-3-fluoropyridine-2-carbonitrile (30 g, 0.15 mol) in methanol (150 ml) at room temperature. 5-Bromo-2-cyano-3-methoxy-pyridine: Mix sodium methoxide (141 mg, 2.61 mmol) and 5-bromo-2- cyano-3-fluoro-pyridine (105 mg, 0.52 mmol) in THF (5 mL) and reflux for 18 h. Add pH 7 phosphate buffer solution and extract with EtOAc. Dry the EtOAc extracts over MgSOTo a stirred solution of 5-bromo-2-cyano-3-nitropyridene (5 g, 0.021 mol) in MeOH (50 mL) at 0°C was added 0.5M sodium methoxide (40 mL) and the RM was heated to reflux and stirred for 8 hr. Afterreaction completion the mixture was concentrated under reduced pressure to give crude 5-bromo-3-methoxypicolinonitrile. The crude was purified by CC (0-15percent EtOAc in PE) and concentrated at below45°C to give 5-bromo-3-methoxypicolinonitrile (3.4 g, 70percent), as a solid.To a solution of 5-bromo-3-nitro-pyridine-2-carbo-nitrile (2 g, 8.8 mmol) in MeOH (25 ml), 0.5 M NaOMe (in MeOH, 15 ml) was added at room temperature. The reaction mixture was heated to reflux and stirred for 8 hours at this temperature. After the reaction completion, the reaction mixture was concentrated under reduced pressure. The residue was purified via column chromatography (Ethyl acetate : n-Hexane = 1 : 4) and the target compound of 1.46 g was obtained. (78percent yield) To a solution of 5-bromo-3-nitro-pyridine-2-carbonitrile (2 g, 8.8 mmol) in MeOH (25 ml), 0.5 M NaOMe (in MeOH, 15 ml) was added at room temperature. The reaction mixture was heated to reflux and stirred for 8 hours at this temperature. After the reaction completion, the reaction mixture was concentrated under reduced pressure. The residue was purified via column chromatography (Ethyl acetate : n-Hexane = 1 : 4) and the target compound of 1.46 g was obtained. (78percentyield)

Molecular Weight:213.03
XLogP3:1.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:211.95853
Monoisotopic Mass:211.95853
Topological Polar Surface Area:45.9
Heavy Atom Count:11
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes