Ammonium formate → HCID 51347781, compound

Participants

Reaction Steps

2-(3,5-Dichloropyridin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[3,4-d]thieno[3,2-b]pyridin-3-one (Example 15, 15 mg, 0.030 mmol), ammonium formate (2.9 mg, 0,046 mmol, 1.5 equiv) and 1,1′-bis(diphenylphosphino)ferroenedichloro palladium (II) dichloromethane complex (4.4 mg, 6.1 lima 0.2 equiv) were combined in methanol (5 mL) and placed into a preheated oil bath at 70° C. for 14 hours. The mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 85:15; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.28 (1H, s), 8.76 (2H, br d, J=5.5 Hz), 8.57 (2H, br d, J=5.5 Hz), 8.48 (1H, d, J=2.5 Hz), 8.16 (1H, d, J=5.6 Hz), 7.84 (2H, d, J=8.6 Hz), 7.73 (1H, d, J=1.5 Hz), 7.68 (1H, d, J=5.6 Hz), 7.53 (2H, d, J=8.6 Hz), 6.53 (1H, dd, J=2.4, 1.8 Hz), 5.77 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 425.1184 [(M+H)+; calculated for C23H17N6OS: 425.1179].

Provenance & Evidence