Sodium Carbonate → 4-(5-Ethoxy-2-fluoro-phenyl)-3,6-dimethyl-pyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-3,6-dimethyl-pyridine-2-carbonitrile (which may be prepared as described in Description 137) (3.82 g, 18.099 mmol) in MeCN (45 mL) and water (5 mL) in a Smith microwave vessel was added (5-ethoxy-2-fluoro-phenyl)boronic acid (3.6627 g, 19.909 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.3811 g, 0.5430 mmol) and sodium carbonate (3.8367 g, 36.198 mmol). The reaction vessel was sealed and purged with nitrogen. The reaction mixture was heated by microwave at 100° C. for 25 min. The reaction mixture was treated with water and was extracted with DCM twice and the organic layers were collected by passing down a PhaseSep cartridge The solvent was removed by evaporation and the residue was purified by silica gel chromatography (100 g SiO2) eluting with ethyl acetate in iso-hexane (10-60%). Evaporation of desired fractions gave 4-(5-ethoxy-2-fluoro-phenyl)-3,6-dimethyl-pyridine-2-carbonitrile (D138) (4.76 g, 17.61 mmol, 97.3% yield);

Provenance & Evidence