Cesium carbonate → HCID 89761912, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-dihydro-2H-benzo[b][1,4]oxazine (500 mg, 3.69 mmol, Tyger Scientific) and 5-chloro-2-fluorobenzonitrile (573 mg, 3.69 mmol) in DMF (10 mL) was added cesium carbonate (3.61 g, 11.0 mmol). The reaction mixture was heated at 100° C. for 24 h. After completion, the reaction mixture was quenched with ice water (10 mL) and extracted with ethyl acetate (2×15 mL). The organic layer was dried over sodium sulfate and concentrated to get crude material which was purified by column chromatography (12 g column: elution: 5% ethyl acetate in hexane) to provide 2-(2h-benzo[b][1,4]oxazin-4(3h)-yl)-5-chlorobenzonitrile (480 mg, 48.4%) as yellow solid. LCMS (ESI) m/z 270.02 (M+H).

Provenance & Evidence