Ammonium formate → HCID 69935115, compound

Participants

Reaction Conditions

Reaction Steps

2-(3,5-Dichloropyridin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H pyrazolo[4,3-c]quinolin-3-one (Example 493, 15 mg, 0.031 mmol), ammonium formate (2.1 mg, 0.34 mmol, 1.1 equiv) and 1,1-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (2.2 mg, 0.00031 mmol, 0.1 equiv) were combined in methanol (2 mL) and placed into a preheated oil bath at 60° C. for 5 hours. The mixture was then heated at 70° C. for an additional 18 hours. The mixture was cooled to ambient temperature, concentrated in vacuo and the residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 8.94 (1H, br m), 8.75 (1H, br m), 8.71 (1H, s), 8.42 (1H, dd, J=7.7, 1.9 Hz), 8.21 (1H, br m), 7.74-7.72 (3H, m), 7.65-7.55 (4H, m), 7.35 (2H, d, J=8.7 Hz), 6.50 (1H, m), 5.62 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 453.1241 [(M+H)+; calculated for C25H18ClN6O: 453.1225].

Provenance & Evidence