methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate → (1H-pyrrolo[2,3-b]pyridin-2-yl)methanol

Participants

Reaction Steps

To an ice-cold solution of methyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (300 mg) in THF (4.5 mL) was added LiAlH4 (1.7 mL, 1M in THF). The ice bath was removed and the reaction mixture was stirred at RT for 2 h. LiAlH4 (2.8 mL, 1M in THF) was added and the stirring was pursued for 20 h at RT. DCM and 1M NaOH were added and the phases were separated. The org. layer was dried (Na2SO4) and evaporated in vacuo to afford 100 mg of oil. LC-MS (B): tR=0.34 min; [M+H]+: 149.28.

Provenance & Evidence