Dimethylformamide → HCID 86588664, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-chloro-7-bromo-1-methyl-1H-pyrazolo[4,3-b]quinoline (EXAMPLE 19, step 2, 1 g, 3.4 mmol), ethyl acrylate (0.42 ml, 3.9 mmol), triethylamine (0.53 ml, 3.8 mmol), palladium acetate (76 mg, 0.34 mmol) and tri-o-tolylphosphine (0.62 g, 2.0 mmol) in N,N-dimethylformamide (80 ml) was stirred at 120° C. for 7 h. The mixture was cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated, diluted with ethyl acetate (50 ml) and washed with saturated aqueous sodium bicarbonate (50 ml). The water layer was extracted with ethyl acetate (50 ml×2) and the organic layers were combined. After dryness over sodium sulfate and evaporation, the residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (1:3) to afford 0.79 g (74%) of the title compound as a pale yellow solid.

Provenance & Evidence