Methanol → N-(2,6-difluorophenyl)-3-{3-[2-({5-fluoro-2-(methyloxy)-4-[2-(1-piperidinyl)ethyl]phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}benzamide

Participants

Reaction Steps

To 2,6-difluoroaniline (133 mg, 1 mmol) was added 1N NaHMDS in THF (1 mL, 1 mmol). The mixture stirred for 15 min at rt. Methyl 3-{3-[2-({5-fluoro-2-(methyloxy)-4-[2-(1-piperidinyl)ethyl]phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}benzoate (120 mg, 0.206 mmol) in 3 mL of dry THF was added. The mixture stirred at rt for 30 min. 1 mL of MeOH was added followed by 1 g of silica gel. The solvent was rotovaped down and the pre-adsorbed solids were purified by flash chromatography to give the title compound (52 mg, 0.0767 mmol, 37%). 1H NMR (400 MHz, CDCl3) δ ppm 9.46 (d, J=7.33 Hz, 1H), 8.21-8.29 (m, 3H), 8.11 (s, 1H), 8.02 (d, J=7.70 Hz, 1H), 7.74-7.83 (m, 2H), 7.66 (d, J=8.80 Hz, 1H), 7.47-7.56 (m, 1H), 7.32-7.40 (m, 1H), 7.22 (dd, J=8.43, 5.87 Hz, 1H), 6.91-7.01 (m, 3H), 6.76 (d, J=6.60 Hz, 1H), 6.63 (dd, J=5.32, 3.12 Hz, 1H), 3.92 (s, 3H), 2.79-2.87 (m, 2H), 2.54-2.61 (m, 2H), 2.45-2.54 (m, 4H), 1.59-1.68 (m, 4H), 1.42-1.52 (m, 2H). MS (ESI): 678 [M+H]+.

Provenance & Evidence