Dimethylacetamide → 1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

Participants

Reaction Steps

Zinc cyanide (900 mg), biphenyl-2-yl(di-tert-butyl)phosphine (610 mg) and zinc (67 mg) were added to a solution of 5-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (1.917 g) in DMA (25 ml), followed by stirring for 5 minutes while degassing under ice cooling, and palladium (II) trifluoroacetate (338 mg) was added thereto, followed by stirring at 80° C. overnight after making it under an argon atmosphere. Ethyl acetate was added thereto, an insoluble substance was separated by celite filtration, and water was added to the filtrate, followed by extraction. The organic layer was washed with a 3M aqueous ammonia solution and then saturated brine in this order and was dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100 to 0:100) to obtain, as a colorless amorphous solid, 1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (377 mg).

Provenance & Evidence