Potassium Carbonate → HCID 66750162, compound

Participants

Reaction Steps

A solution of 5-(6-chloropyridin-2-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (5-2, 55 mg, 0.17 mmol) in DMSO (1 ml), was charged with Potassium carbonate (34.6 mg, 0.25 mmol, 1.5 eq) and 4-Cyanophenol (39.7 mg, 0.33 nmol, 2.0 eq), then irradiated in a microwave at 160 deg C. for 20 min. A second addition of Potassium carbonate (34.6 mg, 0.25 mmol, 1.5 eq) and 4-Cyanophenol (39.7 mg, 0.33 mmol, 2.0 eq) was necessary, then the reaction was irradiated again at 160 deg C. for 20 min. The crude, dark mixture was filtered through a fritted disk, then purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present) to afford the title compound, 4-({6-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]pyridin-2-yl}oxy)benzonitrile (5-3), as an orange oil. 1H NMR (500 MHz, CDCl3) δ 7.80 (t, 1H, J=Hz), 7.71 (d, 2H, J=9.0 Hz), 7.62 (d, 1H, J=7.1 Hz), 7.55 (d, 1H, J=7.3 Hz), 7.51 (s, 1H), 7.34-7.31 (m, 2H), 7.06-7.04 (d, 2H, 8.3 Hz), 6.87 (d, 1H, J=8.1 Hz), 3.68 (s, 2H), 3.44 (s, 3H), 1.04 (s, 9H). LRMS m/z: Calcd for C25H25N4O2 (M+H) 414.2, found 414.3.

Provenance & Evidence