Dimethylformamide → 6-(3,5-dimethylisoxazol-4-yl)-4-(2,2,3,3,3-pentafluoro-1-hydroxypropyl)-1H-benzo[d]imidazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-4-formyl-1H-benzo[d]imidazole-1-carboxylate (100 mg, 0.26 mmol), pentafluoroiodoethane (350 mg, 1.42 mmol) and DMF was cooled to −15° C. under nitrogen. Tetra(dimethlamino)ethylene was added (0.33 mL, 1.42 mmol) and the reaction mixture was irradiated with a sun lamp. A thick precipitate formed, and after 30 minutes, the reaction mixture was diluted with ethyl acetate filtered. The filtrate was washed with water and the organic layer was concentrated and dissolved in ethanol (3 mL) and 4M HCl in dioxane (1 mL) and heated to 70° C. for 1 h. The reaction mixture was concentrated and purified by reverse-phase HPLC to give the desired product as a white powder.

Provenance & Evidence