Acetonitrile → HCID 86645976, compound

Participants

Reaction Steps

Dimethyl-2-oxopropylphosphonate (0.25 ml, 1.2 mmol) was added to a suspension of K2CO3 (0.41 g, 3.0 mmol) and p-toluenesulfonylazide (0.24 g, 1.2 mmol) in CH3CN (15 ml). After stirring for 2 h a solution of (4R)-2-methyl-3-oxo-4-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)pentanal (0.34 g, 1.0 mmol) in CH3OH (5 ml) was added and the resulting mixture was stirred for 8 h at room temperature. The solvents were removed in vacuo and the residue diluted with Et2O (10 ml), washed with water (2×10 ml) and brine (2×5 ml) and dried over anhydrous Na2SO4. After solvent evaporation the crude was pulped in n-pentane to give 2-{4-[(1R)-1-methylprop-2-yn-1-yl]benzyl}-4-(trifluoromethyl)-1,3-thiazole (0.22 g, 0.745 mmol) as a colourless oil (75%). 1H-NMR (CDCl3): δ 8.68 (bs, 1H, NH); 7.85 (d, 2H, J=7 Hz); 7.55 (d, 2H, J=7 Hz); 7.15 (s, 1H), 3.50 (q, 1H, J=7 Hz); 3.25 (s, 1H), 1.50 (d, 3H, J=7 Hz).

Provenance & Evidence