3-Aminophenylboronic acid → 3-Imidazo[1,2-a]pyridin-3-yl-phenylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-imidazo[1,2-a]pyridine (2.7 g, 13.7 mmol) and 3-aminobenzeneboronic acid (2.4 g, 17.5 mmol) in CH3CN (20 ml) and 2N aqueous Na2CO3 (20 ml) was deoxygenated by evacuation then refill with N2 (×3). PdCl2dppf (500 mg, 0.68 mmol) was added and the mixture was deoxygenated again (×3). The reaction was stirred and heated at 80° C. for 8 hours. After cooling to RT the mixture was partitioned between EtOAc/H2O and then filtered through Celite®. The Celite® was washed with CH2Cl2. The layers were separated and the aqueous layer was extracted with CH2Cl2 (×2). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica (100% CH2Cl2→2% 2M NH3-MeOH/CH2Cl2) to give the title compound (1.9 g, solid). MS: [M+H]+ 210

Provenance & Evidence