Sodium Carbonate → HCID 11951661, compound

Participants

Reaction Steps

To a solution of 6-benzyloxy-5-bromo-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide (85 mg) in 1,2-dimethoxyethane (1.6 ml) was added tetrakis(triphenyl-phosphine)palladium(0) (24.5 mg). The mixture was stirred for 10 min. 4-chlorophenyl-boronic acid (37.2 mg) was dissolved in 0.7 ml EtOH and added to the reaction mixture. A solution of Na2CO3 (190 mg) in water (1 ml) was added. The reaction mixture was stirred at 85° C. for 3 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with brine. The org. phase was dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, CH2Cl2=>CH2Cl2MeOH 4:1) to give 6-benzyloxy-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide (50.6 mg) as a white solid. MS (ISP) 437.2 (M+H)+.

Provenance & Evidence