Nitrogen → 6-{4-[1-(4,5-dihydro-oxazol-2-yl)-cyclopropyl]-phenyl}-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Participants

Reaction Steps

Part A. The product of Part A from Example 141 (0.10 g, 0.32 mmol) and 1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.10 g, 0.32 mmol) were dissolved in DMSO (1.5 mL). Potassium carbonate (1.3 g, 0.94 mmol), copper iodide (0.02 g, 0.10 mmol), and 1,10-phenanthroline (0.02 g, 0.11 mmol) were then added and the reaction was heated to 120° C. for 12 h under an environment of N2. The reaction was cooled, diluted with EtOAc, washed with H2O (2×), brine, dried over Na2SO4, filtered, and concentrated to dryness to give 6-{4-[1-(4,5-dihydro-oxazol-2-yl)-cyclopropyl]-phenyl}-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester. LC/MS (ESI+) 501.8 (M+H)+, tR=2.64 min (10–90% CH3CN/H2O in a 4-min run).

Provenance & Evidence