Methylamine → 4-Methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (5.9 g, 17.5 mmol), methyl amine (40 wt. % solution in water, 40 mL) in methoxyethanol (10 mL) is heated at 120° C. in a sealed tube. After overnight, the reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (1N, 20 mL) and heated at 50° C. After stirring for 1.5 hours, the reaction mixture is basified with saturated sodium bicarbonate solution to pH=8. The solid is collected by filtration and washed with water, then hexanes, dried to afford the title compound as a solid. MS m/z 176.2 (M+1).

Provenance & Evidence