Sodium cyanoborohydride → HCID 86689839, compound

Participants

Reaction Steps

A sealed-cap vial was charged with tert-butyl 5-acetyl-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (225 mg, 0.86 mmol), NH4OAc ammonium acetate (666 mg, 8.6 mmol), NaBH3CN (71 mg, 1.1 mmol) and MeOH (7 mL). The reaction was stirred at RT for 24 h, after which additional NH4OAc (333 mg, 4.3 mmol) and NaBH3CN (27 mg, 0.43 mmol) were added. The reaction mixture was stirred for another 24 h then concentrated in vacuo. The residue was partitioned between 2N NaOH and EtOAc. The aqueous layer was thrice extracted with EtOAc. The organic extracts were combined and dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with a mixture of EtOAc containing 1% TEA and MeOH to afford 95 mg (42%) of tert-butyl 5-(1-aminoethyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate: MS (ESI) m/z: 262.2 [M+1]+.

Provenance & Evidence