Perfluoro-1-butanesulfonyl fluoride → 2-(4-tert-Butylphenyl)-N-{(S)-[1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}acetamide

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Reaction Steps

To a solution of 2-(4-tert-Butylphenyl)-N-{(S)-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}acetamide (32.00 mg, 0.0650 mmol) in 0.5 ml of anhydrous CH3CN at RT was added diisopropylethylamine (0.0450 ml, 0.260 mmol), diisopropylethylamine dihydrogen fluoride complex (0.0180 ml, 0.0980 mmol), and perfluorobutanesulfonyl fluoride (0.0230 ml, 0.130 mmol). The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 0.0171 g (53%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.245 (d, J=2.93 Hz, 1H), 7.569 (s, 1H), 7.527 (d, J=7.14 Hz, 1H), 7.369 (m, 2H), 7.270 (m, 1H), 7.225 (m, 2H), 6.336 (d, J=7.14 Hz, 1H), 4.800 (AB q, J=4.53 Hz, 1H), 4.682 (AB q, J=4.21 Hz, 1H), 4.617 (AB q, J=4.53 Hz, 1H), 4.550 (AB q, J=4.67 Hz, 1H), 4.378 (q, J=7.88 Hz, 2H), 3.623 (s, 2H), 3.086 (br s, 1H), 1.314 (s, 9H). ES-MS [M+1]+: 494.2.

Provenance & Evidence