1H-Pyrrolo(2,3-b)pyridine → HCID 178454099, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1H-pyrrolo[2,3-b]pyridine (44.5 mg, 0.377 mmol) in DMF (1.3 ml) at room temperature was added sodium hydride, 60% in oil (18 mg, 0.45 mmol), followed by cis-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (100 mg, 0.38 mmol). The reaction mixture was heated at 100° C. for 16 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was back extracted with EtOAc (2×) and the combined organics was dried (MgSO4) and concentrated. The crude product was purified by ISCO (12 g), eluting with a gradient of EtOAc/hexane 0-50% to provide tert-butyl(trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (10 mg, 0.035 mmol, 9.23% yield) as off-white solid. ESI (M+1) 288.0.

Provenance & Evidence