Triethylamine → 2,2,2-trifluoro-N-{4-[(6-methoxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamide

Participants

Reaction Steps

A flask containing a solution of 29 (0.30 g, 0.85 mmol), Et3N (0.26 g, 2.55 mmol) and DMAP (0.032 g, 0.26 mmol) in CH2Cl2 (5 mL) was added trifluoroethanesulfonyl chloride (0.39 g, 2.13 mmol), dropwise, at RT and the reaction allowed to stir overnight at RT. After 18 h the reaction was diluted with 15 mL CH2Cl2 and rinsed with 10% aq. HCl (25 mL). The CH2CO2 layer was dried (MgSO4), concentrated to a dark amber oil, and purified by silica gel column chromatography with 10% EtOAc/hexanes to afford 270 mg (64%) of the title compound, 273, as a white foam. 1H NMR (400 MHz, DMSO-d6): δ 2.18 (s, 3H), 3.88 (s, 3H), 4.33 (q, J=9.8 Hz, 2H), 6.58 (d, J=9.0 Hz, 2H), 6.98 (d, J=9.0 Hz, 2H), 7.08 (dd, J1=2.4 Hz, J2=9.1 Hz, 1H), 7.18-7.36 (m, 5H), 7.61 (d, J=9.1 Hz, 1H), 7.70 (s, 1H), 10.07 (s, 1H).

Provenance & Evidence