反应详情

4-Fluorobenzenethiol (0.128 ml) was added dropwise to a stirred suspension of sodium hydride (0.049 g of a 60% dispersion in mineral oil) in THF (3 ml). The mixture was stirred for 30 minutes then added dropwise to a stirred and cooled (−65° C.) solution of 3-acetamido-2-amino-4-fluoronitrobenzene (0.233 g) in THF (2 ml). The mixture was stirred for 3 hours at −65° C. then allowed to warm to ambient temperature. Saturated aqueous ammonium chloride solution (5 ml), then water (5 ml) were added and the mixture was extracted with ether (2×25 ml). The extracts were combined, washed with water (25 ml) and brine (25 ml), then dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column eluting with 0-40% EtOAc/isohexane to give the title compound. Chromatography on a Biotage cartridge (40 g silica), eluting with 40% EtOAc/isohexane to give the title compound (0.193 g) as a solid. NMR: 2.14 (s, 3H), 6.76 (d, 1H), 7.4 (t, 2H), 7.6 (m, 2H), 7.88 (d, 1H), 10.1 (brs, 1H); m/z: 339.

1. additionthen added dropwise to
2. stirringa stirred
3. stirringThe mixture was stirred for 3 hours at −65° C.
4. extractionthe mixture was extracted with ether (2×25 ml)
5. washwashed with water (25 ml) and brine (25 ml)
6. customdried
7. customVolatile material was removed by evaporation
8. customthe residue was purified on a silica gel Mega Bond Elut column
9. washeluting with 0-40% EtOAc/isohexane