Dimethylformamide → HCID 69825004, compound

Participants

Reaction Conditions

Reaction Steps

Triisopropylsilane thiol (2.0 ml) was added to a stirred suspension of sodium hydride (0.37 g, 60% mineral oil dispersion) in anhydrous THF (30 ml) cooled to 0° C. under argon. After 20 minutes at this temperature the reaction mixture was added to a stirred suspension of (R)-N-[4-iodo-2,3-dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 4) (4.0 g) and tetrakis(triphenylphosphine)palladium(0) (0.86 g) in anhydrous toluene (40 ml). The mixture was heated to 85° C. for 5 hours and DMF (10 ml) was added to obtain a clear solution. Heating was continued for a further 17 hours. The mixture was allowed to cool to ambient temperature, EtOAc (200 ml) was added and the mixture washed with brine (3×100 ml) and dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography eluting with 1-50% EtOAc/isohexane to give the title compound (0.448 g) as an orange solid. NMR: 1.58 (s, 3H), 7.55 (d, 1H), 7.66 (d, 1H), 7.73 (s, 1H), 9.80 (s, 1H); m/z: 332.

Provenance & Evidence