3-Bromo-1-propanol → HCID 69749686, compound

Participants

Reaction Steps

Sodium hydride (0.06 g of a 60% dispersion in oil) was added to a solution of (R)-N-[2-chloro-4-(4-hydroxyphenylsulphinyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 89) (0.5 g) in DMF (5 ml) at 0° C. The mixture was stirred for 15 minutes then 3-bromopropanol (0.12 ml) was added as a solution in DMF (3 ml). The mixture was stirred at ambient temperature for 16 hours. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-10% methanol/DCM to give the title compound (0.34 g) as a gum. NMR (CDCl3): 1.25 (dd, 2H), 1.7 (s, 3H), 1.8 (s, 1H), 3.8-3.9 m, 2H), 4.1-4.2 (m, 2H), 5.1 (s, 1H), 6.95 (d, 2H), 7.4 (d, 1H), 7.5 (d, 2H), 7.6-7.65 (m, 1H), 8 45-8.55 (m, 1H), 9.3 (s, 1H); MS (ESP−): 464.

Provenance & Evidence