Potassium Phosphate, Tribasic → 8-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A suspension of 8-chloro-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (250 mg, 1.2 mmol), 4-cyclobutyl-2-fluoroaniline (230 mg, 1.4 mmol), Pd2dba3 (43 mg, 0.047 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (80 mg, 0.19 mmol) and K3PO4 (350 mg, 1.7 mmol) in toluene (5 ml) was degassed with argon for 10 minutes and then heated at 100° C. for 18 hours. The reaction mixture was then cooled to room temperature and filtered through hyflo®. The filtrate was concentrated in vacuo, and the resultant gum was subjected to flash chromatography (Si-PPC, eluting with 5% ethyl acetate in DCM) to afford the title compound as a yellow oil (150 mg, 38%). 1H NMR (CDC13): 7.95 (1H, s), 7.73 (1H, d, J=7.4 Hz), 7.23 (1H, t, J=8.6 Hz), 7.07 (1H, d, J=7.3 Hz), 7.01 (2H, m), 6.50 (1H, s), 3.90 (3H, s), 3.59 (1H, m), 2.39 (2H, m), 2.17 (2H, m), 2.06 (1H, m), 1.93 (1H, m).

Provenance & Evidence