3-(Trifluoromethyl)phenyl isocyanate → HCID 59427911, compound

Participants

Reaction Steps

To a solution of 3-iodoindole (583 mg, 2.4 mmol) (Witulski, B.; Buschmann, N.; Bergstrasser, U. Tetrahedron 2000, 56, 8473-8480.) in DMF (10 mL) at 0° C. was added NaH (125 mg, 3.1 mmol, 60% dispersion in mineral oil). The reaction mixture was allowed to warm to room temperature and stir for 0.5 h. Then 1-isocyanato-3-(trifluoromethyl)benzene (0.38 mL, 2.64 mmol) was added and allowed to stir for an additional 0.5 h. Sat. aq. NH4Cl (20 mL) was added and the mixture was poured onto water (50 mL). The aqueous layer was extracted with Et2O (3×25 mL). The combined organics were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude concentrate was purified via automated flash chromatography (silica gel, 0 to 50% EtOAc in hexanes, gradient elution) to afford 3-iodo-N-(3-(trifluoromethyl)phenyl)-1H-indole-1-carboxamide.

Provenance & Evidence