6-Azaindole → tert-Butyl 4-{1H-pyrrolo[2,3-c]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate

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Reaction Steps

A suspension of 1H-pyrrolo[2,3-c]pyridine (0.95 g, 8.05 mmol), tert-butyl 4-oxo-piperidine-1-carboxylate (1.70 g, 8.54 mmol) and KOH (0.95 g, 17.0 mmol) in MeOH (10 mL) was heated at reflux overnight. The mixture was added to ice-water (50 mL) and then MeOH (50 mL) was added. The resulting solution was concentrated to circa 50 mL and then extracted three times with DCM/MeOH (9:1, 50 mL). The organic layers were combined and concentrated and the residue was purified by flash chromatography (9:1 DCM/MeOH) to yield the title compound as a light yellow solid (2.21 g, 92%). MS (ESI+) m/z=300 (M+H)+.

Provenance & Evidence