Dichloromethane → N-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenyl)-7-(6-formylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture comprising 7-bromo-N-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide (Intermediate 3A) (2.7 g, 5.36 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinaldehyde (1.375 g, 5.90 mmol) and cesium carbonate (6.99 g, 21.46 mmol) in DME (30 ml) and water (3 ml) was treated with PdCl2(dppf).CH2Cl2 adduct (0.219 g, 0.268 mmol). The mixture was placed under nitrogen and heated at 100° C. for 1 hr. The resulting mixture was concentrated in vacuo and the residue was dissolved in 10% trifluoroethanol/CHCl3. The organics were washed with water and NaHCO3 and concentrated in vacuo. Purification by chromatography on silica eluting with 0-30% 2M NH3 in MeOH/DCM afforded the title product;

Provenance & Evidence