Cesium carbonate → HCID 67958593, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-5-iodopyridine (500 mg, 1.761 mmol, Aldrich), tert-butyl 3-aminopiperidine-1-carboxylate (388 mg, 1.937 mmol, Combi-blocks), Cut (33.5 mg, 0.176 mmol, Aldrich) and cesium carbonate (1148 mg, 3.52 mmol, Fluka) was capped, degassed and backfilled with argon (3×). Dioxane (2 mL) and 2-isobutyrylcyclohexanone (0.118 mL, 0.704 mmol) were added, and the reaction was heated to 55° C. After 16 h, the temperature was raised to 70° C. After 60 h at 70° C., the reaction mixture was cooled to 23° C., diluted with EtOAc (75 mL) and washed with brine (50 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 25-60% EtOAc/hexane), affording tert-butyl 3-(5-bromopyridin-3-ylamino)piperidine-1-carboxylate (375 mg, 60%). MS (ESI, pos. ion) m/z: 356.1 (M+1), 358.1 (M+3).

Provenance & Evidence