Toluene → 3-(5-Ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile

Participants

Reaction Steps

A mixture of 5-bromo-3-ethyl-2-methoxy-4,6-dimethylpyridine (254 mg, 1.75 mmol), 3-cyanophenylboronic acid (254 mg, 1.75 mmol), palladium tetrakis(triphenylphosphine) (81.2 mg, 0.07 mmol), 2M aq sodium carbonate (1.15 mL), toluene (10 mL) and methanol (0.7 mL) is reacted following the procedures of Step 4, Example 5. The crude product is purified by HPLC in two runs eluting with a gradient of acetonitrile-20 to 5% water ramping @ 0.5% per min. Product containing fractions from both runs are combined and concentrated to afford 3-(5-ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile (44 mg, 14%) as an oil. LC/MS: MS m/e=267 (M+H); RT 4.41 min.

Provenance & Evidence