2,6-Difluoroaniline → HCID 59452831, compound

Participants

Reaction Steps

To methyl 5-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)-2-(methyloxy)benzoate (2.35 g, 4.36 mmol) and 2,6-difluoroaniline (2.35 mL, 21.8 mmol) in THF (30 mL) was added sodium bis(trimethylsilyl)amide (26.0 mL, 1M in THF, 26.0 mmol) in one portion. Upon completion by MS, the reaction was poured into half saturated NaHCO3, extracted with DCM and EtOAc, dried (MgSO4) and concentrated. Purification by flash chromatography and trituration with diethyl ether provided the title compound (2.05 g, 3.23 mmol, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.16 (s, 6H), 2.56 (br. s., 2H), 3.98 (br. s., 5H), 6.55 (d, J=7.7 Hz, 1H), 6.69 (d, J=4.4 Hz, 1H), 7.01-7.11 (m, 1H), 7.17 (d, J=7.3 Hz, 3H), 7.27 (s, 2H), 7.32-7.42 (m, 1H), 7.42-7.54 (m, 2H), 7.74 (d, J=8.8 Hz, 1H), 7.81 (d, J=8.1 Hz, 1H), 8.15 (s, 1H), 8.37 (d, J=4.4 Hz, 1H), 9.49 (br. s., 1H), 9.78 (d, J=12.5 Hz, 2H). MS (M+H, ES+) 636.

Provenance & Evidence