Diisopropylethylamine → HCID 53469265, compound

Participants

Reaction Steps

A solution of 7-chloro-3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine (58.9 mg, 0.206 mmol), (2,5-difluorophenyl)acetic acid (35.5 mg, 0.206 mmol), HATU (78 mg, 0.206 mmol), and DIEA (0.036 mL, 0.206 mmol) in N,N-Dimethylformamide (DMF) (3 mL) was stirred overnight at room temperature. LCMS analysis at this time indicated good conversion, so the reaction mixture was poured into water (10 mL) and stirred for one hour. The resulting precipitate was collected by filtration, dried at the pump for an hour, adsorbed onto silica and purified by flash chromatography (0-10% MeOH in EtOAc) to afford 7-chloro-3-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridin-4-amine (67 mg, 73.9% yield) as a white solid. LC-MS (ES) m/z=440, 442 [M+H]+. 1H NMR (400 MHz, DMSO-d6) ppm 3.29 (t, J=8.46 Hz, 2H), 3.96 (s, 2H), 4.31 (t, J=8.34 Hz, 2H), 5.72 (s, 2H), 7.13-7.34 (m, 4H), 7.41 (s, 1H), 7.92 (s, 1H), 8.07 (s, 1H), 8.13 (d, J=8.34 Hz, 1H).

Provenance & Evidence