2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 25106933, compound

Participants

Reaction Steps

To an ambient solution of Example 8B (0.02 g, 0.062 mmol) in tetrahydrofuran (1 mL) was added 2-fluoro-5-trifluoromethylphenylisocyanate (0.010 g, 0.065 mmol). After 1 h, the mixture was concentrated under reduced pressure. The residue was purified by RP-HPLC (preparative reversed-phase high pressure liquid chromatography) using a Zorbax SB-C18 7M 21.2×250 mm column with UV detection analyzed at 220 and 254 nM (preparative method: water with 0.1% trifluoroacetic acid and CH3CN with 0.1% trifluoroacetic acid gradient 5-95% CH3CN over 30 minutes at 15 mL/min). The fractions containing the desired product were diluted with saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.01 (t, J=7.1 Hz, 3H), 1.73 (br d, J=11.9 Hz, 2H), 2.08 (dt, J=11.9 and 3.7 Hz, 2H), 2.25-2.37 (m, 4H), 2.64-2.73 (m, 2H), 6.15 (s, 1H), 7.33-7.52 (m, 3H), 7.61 (m, 1H), 8.05 (s, 1H), 8.24 (m, 1H), 8.64 (m, 1H), 8.90 (s, 1H), 9.34 (s, 1H); MS (ESI) m/z 527 [M+H]+.

Provenance & Evidence