5-Chloro-2-fluoroaniline → HCID 59452617, compound

Participants

Reaction Steps

A 1.0M solution of NaHMDS in THF (0.59 mL, 0.59 mmol) was added dropwise to a stirring solution of methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzoate (0.100 g, 0.20 mmol) and 5-chloro-2-fluoroaniline (0.09 g, 0.59 mmol) in THF (2 mL) at rt. The reaction mixture was stirred for 0.5 h at room temperature then quenched with methanol and concentrated onto silica gel. Flash chromatography afforded the title compound (0.115 g, 94%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 10.31 (s, 1H), 9.75 (s, 1H), 9.52-9.50 (m, 1H), 8.35 (d, J=5.2 Hz, 1H), 8.31 (s, 1H), 8.01 (d, J=7.7 Hz, 1H), 7.83 (d, J=7.7 Hz, 1H), 7.77-7.72 (m, 2H), 7.61-7.57 (m, 1H), 7.51-7.47 (m, 2H), 7.36-7.24 (m, 3H), 7.17-7.06 (m, 2H), 6.60 (d, J=5.3 Hz, 1H), 6.53 (dd, J=8.2, 2.4 Hz, 1H), 3.95 (t, J=5.9 Hz, 2H), 2.55 (t, J=5.7 Hz, 2H), 2.14 (s, 6H). MS (ES+, m/z) 622 (M+1).

Provenance & Evidence