Sodium Carbonate → HCID 21905722, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (RS)-2-(4-bromo-2-fluoro-phenyl)-N-(4-cyano-benzyl)-2-methoxy-acetamide (example 41.2, 173 mg) in 1,2-dimethoxyethane (8 ml) were added PdCl2(dppf) (34 mg), an aqueous 10% solution of Na2CO3 (2 ml) and 4-dimethylaminophenylboronic acid (378 mg). The mixture was then stirred at 85° C. under an argon atmosphere for 1.5 h. After cooling to rt, the mixture was diluted with ethyl acetate (15 ml) and washed with water (10 ml). The aqueous layer was extracted with ethyl acetate and the combined organics were washed with water and brine, dried (MgSO4), filtered and concentrated. The product was purified by chromatography (silica gel, gradient cyclohexane=>cyclohexane/ethyl acetate 2:3) to give (RS)-N-(4-cyano-benzyl)-2-(4′-dimethylamino-3-fluoro-biphenyl-4-yl)-2-methoxy-acetamide (167 mg) as a light yellow solid.

Provenance & Evidence