Potassium Carbonate → HCID 66749493, 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, 23 mg, 0.07 mmol) in DMSO (2 ml) was charged with Potassium carbonate (20.5 mg, 0.15 mmol, 2.0 eq) and 2-Chloro-3-cyanopyridine (15.4 mg, 0.11 mmol, 1.5 eq). The mixture was irradiated in a microwave at 160 deg C. for 20 min. The resulting dark mixture was purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present), providing the title compound, 2-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]phenoxy} nicotinonitrile (2-1), as a tan solid-oil. 1H NMR (400 MHz, CDCl3) δ 8.34 (d, 1H, J=3.3 Hz), 8.03 (d, 1H, J=5.9 Hz), 7.51-7.50 (m, 2H), 7.42 (s, 1H), 7.32 (d, 1H, J=8.2 Hz), 7.20-7.17 (m, 2H), 7.13-7.09 (m, 2H), 3.70 (s, 2H), 3.49 (s, 3H), 1.06 (s, 9H). LRMS m/z: Calc'd for C25H24N4O2(M+H) 413.4, found 413.2.

Provenance & Evidence