2-Fluoro-5-methylphenyl isocyanate → 4-[3-(2-Fluoro-5-methylphenyl)ureidophenyl]-1H-indole-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

0.115 cm3 (0.876 mmol) of 2-fluoro-5-methylphenyl isocyanate is added, at a temperature in the region of 20° C., under an argon atmosphere, to 0.2 g (0.796 mmol) of 3-(4-aminophenyl)-1H-indole-2-carboxamide in solution in 10 cm3 of tetrahydrofuran. After stirring for 18 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), to give 400 mg of a residue which is purified by flash chromatography [eluent: ethyl acetate/cyclohexane (7/3 by volume)]. After concentration under reduced pressure of the fractions containing the expected product, 250 mg of a yellow residue are obtained, which residue is stirred in 10 cm3 of dichloromethane and then filtered and dried under reduced pressure (2.7 kPa), to give 180 mg of 3-{4-[3-(2-fluoro-5-methylphenyl)ureido]phenyl}-1H-indole-2-carboxamide, in the form of a beige solid that melts at 220° C.;

Provenance & Evidence