Iodoethane → HCID 24825701, compound

Participants

Reaction Steps

To a solution of [3-(3,3-difluoro-2,2-dimethyl-indan-1-yl)-3H-imidazol-4-yl]-methanol, (160 mg, 0.575 mmol) in DMF (5 mL) is added a 60% dispersion of NaH in oil (46 mg, 1.15 mmol). The reaction is permitted to stir for 30 minutes at room temperature, at which time iodoethane (0.05 mL, 0.63 mmol) is added. The reaction is permitted to stir for 2 hours at which time it is diluted with saturated aqueous NaHCO3 and ethyl acetate. The layers are separated and the organic layer is dried with Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1:6) to furnish 1-(3,3-difluoro-2,2-dimethyl-indan-1-yl)-5-ethoxymethyl-1H-imidazole; HRMS: (ESI) m/z 307.1634 [(M+H)+: Calcd for C17H21N2OF2: 307.1622]; 1H NMR (400 MHz, CDCl3) δ ppm 0.94 (d, J=2.5 Hz, 3 H), 1.28 (t, J=7.1 Hz, 3 H), 1.33 (d, J=3.3 Hz, 3 H), 3.51-3.68 (m, 2 H), 4.54-4.70 (m, 2 H), 5.58 (br. s., 1 H), 7.19 (s, 1 H), 7.23-7.26 (m, 1 H), 7.34 (s, 1 H), 7.55-7.63 (m, 2 H), 7.69-7.76 (m, 1 H).

Provenance & Evidence