Diiodomethane → 2-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Participants

Reaction Steps

TMSCl (0.1 mL) was added to a suspension of zinc (1.2 g, 18.3 mmol) and lead (II) iodide in tetrahydrofuran at room temperature. After stirring at room temperature for 10 min, diiodomethane (0.653 mL) was added dropwise maintaining the reaction at a gentle reflux. After stirring 1 h, the reaction mixture was cooled to 0° C., TiCl4 (1 M in DCM) (2.02 mL) was added dropwise. After stirring at room temperature for 1 h, a solution of intermediate 7 (238 mg, 0.54 mmol) in tetrahydrofuran was added and the reaction monitored by LCMS. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organics were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford 2-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide which was used in the subsequent step without further purification.

Provenance & Evidence