Cesium carbonate → HCID 11693265, compound

Participants

Reaction Conditions

Reaction Steps

3-Fluoro-4-{-(1R)-1-[({1-[(trifluoroacetyl)amino]cyclopropyl}carbonyl)amino]ethyl}-phenylboronic acid (0.050 g, 0.138 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.013 g, 0.014 mmol), and cesium carbonate (0.054 g, 0.166 mmol) were added to a flame-dried flask under argon. 2-chloro-6-{[(trifluoromethyl)sulfonyl]oxy}phenyl trifluoromethanesulfonate (0.068 g, 1.66 mmol) as a solution in dioxane (0.33M) and tri-tert-butyl phosphine (0.007 g, 0.035 mmol) as a solution in dioxane (1.65M) were added to the solids and heated at 85° C. After 1.5 hours the reaction was diluted with methanol, filtered and purified by reverse phase chromatography using a gradient from 95/5H2O/CH3CN to 5/95H2O/CH3CN. The product was lyophilized to yield the title compound as a solid. High resolution mass spectrometry: C22H16F10N2O8S2 requires: 691.0261, found: 691.0275. 1H NMR (400 MHz, (CD3)2SO) δ 9.80 (s, 1H), 8.32 (d, J=7.4 Hz, 1H), 7.86-7.92 (m, 1H), 7.76-7.81 (m, 2H), 7.53 (t, J=7.9 Hz, 1H), 7.37 (dd, J=11 Hz, J=1.7 Hz, 1H), 7.33 (dd, J=7.9 Hz, J=1.7 Hz, 1H), 5.24 (qn, J=7.4 Hz, 1H), 1.41 (d, J=7.4 Hz, 3H), 1.30-1.37 (m, 2H), 0.92-1.08 (m, 2H).

Provenance & Evidence