3-Bromo-1,1,1-trifluoro-2-propanone → HCID 86640275, compound

Participants

Reaction Steps

To a solution of 2-{3-[(aminocarbonothioyl)amino]phenyl}-2-fluoropropanoate (0.84 g, 3.3 mmol) in a 1:1 dioxane/water mixture (10 mL), 3-bromo-1,1,1-trifluoroacetone (0.42 mL, 4.0 mmol) was added dropwise and the mixture refluxed for 18 h. After cooling at room temperature, a saturated solution of NaHCO3 (20 mL) was added and the mixture trasferred into a separator funnel; the aqueous phase was extracted with EtOAc (3×20 mL) and the collected organic extracts dried over Na2SO4 and evaporated under vacuum to give a crude that, after purification by flash chromatography, afforded pure methyl 2-fluoro-2-(3-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate as yellow solid (0.89 g, yield 77%). 1H-NMR (CDCl3) δ 7.95 (bs, 1H, NH), 7.53 (s, 1H), 7.42 (m, 2H), 7.28 (s, 1H), 7.10 (s, 1H), 3.80 (s, 3H), 1.95 (d, 3H, J=23 Hz).

Provenance & Evidence