Dimethylformamide → HCID 23074614, compound

Participants

Reaction Conditions

Reaction Steps

A 2 M solution (10 ml) of lithium diisopropylamide in heptane-THF-ethylbenzene was added to tetrahydrofuran (20 ml) under argon atmosphere, and the mixture was cooled to −78° C. in a dry ice-acetone bath. To the resultant solution was added dropwise over 30 minutes a solution of 4,6-dimethyl-1-(1,2,3,4-tetrahydro-1-naphthyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (3.0 g, 10 mmol) in tetrahydrofuran (30 ml), and after completion of the dropwise addition, the reaction mixture was stirred at −78° C. for 30 minutes. Next, DMF (3.1 ml, 40 mmol) was added thereto, the dry ice-acetone bath was removed, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was distributed to ethyl acetate and water. The organic extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum. To the residue was added hexane, and the residue was finely crushed using a spatula. The solid material was collected by filtration and washed with hexane to give the title compound (yield (amount) 2.7 g, yield (rate) 82%).

Provenance & Evidence