Tetrahydrofuran → 1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (2.0 g, 10 mmol) in anhydrous THF (50 mL) at −70° C. under nitrogen was added n-butyl lithium (2.5 M in hexane, 50 mmol) and the reaction mixture was stirred for 1 h at −70° C. The resulting orange gel was quenched with methyl formate (10 mL) and the reaction mixture was slowly warmed to RT. The mixture was poured into water (20 mL) and extracted with EtOAc (2×250 mL). The organic layers were combined, dried (Na2SO4), filtered, and concentrated to afford 500 mg, (33%) of 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde as yellow solid. MS (ESI) m/z: 147.2 [M+1]+.

Provenance & Evidence