Cesium carbonate → HCID 67026106, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 63 (200 mg, 0.66 mmol) and pyrrolidin-2-one (Aldrich, 85 mg, 0.99 mmol) in toluene (anhydrous 10 mL) was degassed and purged with nitrogen three times, cesium carbonate (Aldrich, 324 mg, 0.993 mmol) and tris(dibenzylideneacetone)dipalladium(0) (Aldrich, 12.1 mg, 0.013 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Aldrich, 23.0 mg, 0.040 mmol, xantphos) were added, degassed and purged with nitrogen three times. The mixture was then heated to 100° C. and stirred under nitrogen for 15 hours. It was then cooled to ambient temperature and diluted with ethyl acetate (50 mL), washed with brine (2×5 mL), concentrated, purified with chromatography (v. ethyl acetate/hexane=1/1, Rf=0.1) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.04-2.19 (m, 2H), 2.57 (t, J=7.9 Hz, 2H), 3.95 (t, J=6.9 Hz, 2H), 7.60-7.75 (m, 2H), 7.84-8.10 (m, 2H), 8.46 (dt, J=7.9, 2.0 Hz, 1H), 8.64 (t, J=2.0 Hz, 1H), 8.82 (dd, J=5.0, 1.8 Hz, 1H), 9.26 (dd, J=2.4, 0.8 Hz, 1H) ppm; MS (DCI/NH3) m/z 307 (M+H)+.

Provenance & Evidence