Methanol → HCID 118590573, compound

Participants

Reaction Conditions

Reaction Steps

To stirred solution of 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyridin-2-amine (0.3 g, 1.0 mmol) (from Int-15) in dry toluene (3 ml, 10 v) was added DMF-DMA (0.14 g, 1.2 mmol) under N2 atm and stirred for 2 h at 120° C., after completion of starting material; cooled it to 10° C. then added 2-bromo-1-(4-fluorophenyl)ethanone (0.3 g, 1.4 mmol) drop wise and methanol (1 ml) was added under N2 atm then stirred for 16 h at 120° C. Reaction mixture was cooled to room temperature and solvent was removed under vacuum and residue was dissolved in DCM (100 ml), washed with water, brine and dried over Na2SO4 and concentrated under vacuum to get crude product. Crude was purified by column chromatography using 60-120 mesh silica gel product eluted with 30-40% ethyl acetate/Hexane to afford (6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridin-3-yl)(4-fluorophenyl)methanone as a off white solid (0.02 g, 4.3% Yield), MS (ESI): m/z 423.1 (M+H). 1H NMR (300 MHz, CDCl3) δ 9.08 (1H, s), 8.04 (1H, s), 7.89-7.84 (2H, m), 7.59-7.56 (1H, d J=9 Hz), 7.23-7.17 (2H, m), 7.09-7.08 (1H, m), 6.96-6.92 (2H, m), 6.81 (1H, bs), 5.07-5.04 (1H, d J=9 Hz), 3.85-3.75 (1H, m), 3.49-3.47 (1H, m), 2.54-2.46 (1H, m), 2.14-2.08 (3H, m) ppm.

Provenance & Evidence