Cesium carbonate → HCID 66749484, compound

Participants

Reaction Steps

A solution of 1-(2,2-dimethylpropyl)-5-(3-hydroxyphenyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-179, 70 mg, 0.23 mmol) and Cesium carbonate (73.5 mg, 0.23 mmol, 1.0 eq) in N-Methylpyrrolidine (1 ml) was stirred at 23 deg C. for 45 min. 4-Bromobenzonitrile and Copper (I) Chloride were added and the resulting mixture was irradiated in a microwave at 150 deg C. for 5 min. LC/MS analysis showed very little conversion, so the reaction was capped and heated in an oil bath at 175 deg C. for 16 h. The resulting crude, dark mixture was run through a filter disk, then purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present), providing 4-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]phenoxy}benzonitrile (4-1) as a tan solid-oil. 1H NMR (400 MHz, CDCl3) δ 7.62 (d, 2H, J=8.7 Hz), 7.48-7.47 (m, 2H), 7.30-7.28 (m, 2H), 7.08 (s, 1H), 7.08-7.02 (m, 4H), 3.69 (s, 2H), 3.47 (s, 3H), 1.06 (s, 9H). LRMS m/z: Calc'd for C26H25N3O2(M+H) 412.5, found 412.3.

Provenance & Evidence