Sodium hydride → HCID 66749106, compound

Participants

Reaction Steps

A solution of 6-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-4, 500 mg, 2.20 mmol) in DMF (10 ml) was treated with Sodium hydride (176 mg, 4.40 mmol, 2.0 eq) followed by the 1-Iodo-2,2-Dimethylpropane (585 pt, 4.40 mmol, 2.0 eq). The reaction was irradiated at 175 deg C. for 20 min in a microwave. The reaction was complete by LC/MS, so it was partitioned between EtOAc (2×125 ml) and water (150 ml). The combined organic layers were dried over Na2SO4 and concentrated. The crude maroon-orange oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc), affording the title compound, 5-bromo-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-5), as a yellow solid with >95% purity. 1H NMR (600 MHz, CDCl3) δ 7.18 (dd, 1H, J=Hz), 7.10 (s, 1H), 6.88 (d, 1H, J=Hz), 3.63 (s, 2H), 3.40 (s, 3H), 1.02 (s, 9H). LRMS m/z: Calc'd for C7H7BrN2O2 (M+H) 232.1, found 232.8.

Provenance & Evidence