反应详情

To a nitrogen flushed mixture of 3-cyanophenylboronic acid (5.0 g, 34 mmol), 3-bromo-6-methoxy-2-methylpyridine (4.6 g, 22.7 mmol) and palladium tetrakis(triphenylphosphine) (789 mg, 0.68 mmol) is added toluene (150 mL), methanol (12 mL) and sodium carbonate (22.7 mmol) and the mixture is heated overnight at reflux. The cooled reaction is concentrated and the residue is purified by chromatography eluting with cyclohexane-3.2 to 9% ethyl acetate. Product containing fractions are combined and concentrated to afford 3-(6-methoxy-2-methylpyridin-3-yl)benzonitrile (3.09 g, 61% yield) as a white solid. LC/MS: MS m/e=225 (M+H); RT 3.58 min; 1H NMR (CDCl3, δ ppm) 7.65 (1H, m), 7.60 (1H, m), 7.56 (2H, m), 7.40 (1H, d), 6.63 (1H, d), 3.98 (3H, s), 2.40 (3H, s).

1. customTo a nitrogen flushed
2. temperaturethe mixture is heated overnight
3. temperatureat reflux
4. customThe cooled reaction
5. concentrationis concentrated
6. customthe residue is purified by chromatography
7. washeluting with cyclohexane-3.2 to 9% ethyl acetate
8. additionProduct containing fractions
9. concentrationconcentrated