2-Aminothiazole → 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a vial charged with perfluorophenyl 5-(2-chloro-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate (0.200 g, 0.362 mmol) and THF (1 mL), was added thiazol-2-amine (0.040 g, 0.398 mmol) as a solution in THF (2 mL). The solution was cooled to −78° C., and a THF solution of lithium bis(trimethylsilyl)amide (0.724 ml, 0.724 mmol, 1M) was added dropwise by syringe. The solution was maintained at −78° C. for 5 min and then allowed to warm to rt. The solution was concentrated and the crude residue was absorbed onto a 5 g plug of silica gel and purified by chromatography through a silica gel column (40 g), eluting with a gradient of 5% to 90% EtOAc in hexane, to provide 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (0.112 g, 0.239 mmol) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 6.83 (d, J=4.59 Hz, 1H) 7.24 (d, J=4.59 Hz, 1H) 7.47 (d, J=8.98 Hz, 1H) 7.60 (d, J=7.16 Hz, 1H) 7.66-7.83 (m, 3H) 7.88 (d, J=8.23 Hz, 1H) 8.09 (s, 1H) 8.29 (d, J=8.33 Hz, 1H) 8.56 (d, J=1.71 Hz, 1H) 12.80 (br. s., 1H); m/z (ESI, +ve ion) 468.9 (M+H)+.

Provenance & Evidence