Diethyl Ether → 1-(5-(1-Aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)azetidin-3-ol

Participants

Reaction Steps

To a solution of 6-(3-hydroxyazetidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (2.6 g, 11 mmol) in THF 100 mL at 0° C. was slowly added 3M methylmagnesium bromide in ether (15.2 mL, 45.6 mmol) to give a yellow solution. After 1 hour, the reaction mixture was warmed to RT and was stirred for an additional 2.5 hours. The reaction was then quenched with MeOH (5 mL). The mixture was stirred for 15 minutes. Sodium borohydride (0.862, 22.8 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was subsequently quenched with 1M HCl (5 mL). The mixture was stirred for 15 minutes, diluted with EtOAc, and washed with saturated aqueous NH4Cl (3×). The aqueous layer was concentrated to give the title compound as a brown solid, which was used without further purification.

Provenance & Evidence