Potassium Carbonate → HCID 10282458, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 61 mg (0.1 mmol) N-({3-[(5-bromo-2-methoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in 2 mL toluene is treated with 4 mg (0.003 mmol) tetrakis(triphenylphosphine)palladium(0), 15 mg (0.12 mmol) pyridine-3-boronic acid and 0.2 mL 2M potassium carbonate. The solution is heated to 85° C. for 18 hr and cooled to room temperature. The solution is diluted with 10 mL dichloromethane, washed with 10 mL brine, dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude residue. The residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH) to afford 55 mg (89%) (2-chloro-3,4-dimethoxyphenyl)-N-({3-[(2-methoxy-5-(3-pyridyl)phenyl)methyl](imidazol[1,2-a]pyridin-2-yl)}methyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 613.

Provenance & Evidence