3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → 3-[6-(4-Fluoro-phenyl)-pyrazolo[1,5-a]pyridin-3-yl]phenylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(4-fluoro-phenyl)-3-iodo-pyrazolo[1,5-a]pyridine (140 mg, 0.41 mmol) and 3-aminophenylboronic acid pinacol ester (120 mg, 0.5 mmol) in DME (2 ml) and 2N Na2CO3 (aq, 2 ml) was deoxygenated by evacuation/refill with N2 (×3). PdCl2ddpf (15 mg, 0.02 mmol) was added and the mixture was deoxygenated again (×2). The reaction was stirred and heated at 90° C. under N2 for 24 hours. After cooling to RT the mixture was partitioned between CH2Cl2/H2O. The layers were separated using a phase separating cartridge. The organic layer was evaporated and the residue was purified by chromatography on silica (25→65% EtOAc/Petrol) to give the title compound (55 mg, solid).

Provenance & Evidence