Triphenylphosphine → HCID 86686103, compound

Participants

Reaction Steps

An orange 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) in Dichloromethane (10 ml) was treated with polymer bound-Triphenylphosphine (177 mg, 0.68 mmol, 3.0 eq) and the 2-Fluorobenzyl alcohol (56.9 mg, 0.45 mmol, 2.0 eq). The mixture was charged, in portions, with Di-tert-butyl azodicarboxylate (104 mg, 0.45 mmol, 2.0 eq) and the resulting maroon-orange solution was stirred at 23 deg C. for 1 h. The reaction mixture was filtered through a frit and the filtrate was purified via flash column chromatography (SiO2: 100% Hex to 75:25% Hex:EtOAc) to afford the title compound, 1-(2,2-dimethylpropyl)-5-{3-[(2-fluorobenzyl)oxy]phenyl}-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (3-1), as an orange oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (t, 1H, J=7.0 Hz), 7.38-7.26 (m, 3H), 7.22-7.15 (m, 3H), 7.13-7.06 (m, 3H), 6.97 (d, 1H, J=7.1 Hz), 5.21 (s, 2H), 3.68 (s, 2H), 3.47 (s, 3H), 1.06 (s, 9H). LRMS m/z: Calc'd for C26H27FN2O2 (M+H) 419.2, found 419.3.

Provenance & Evidence