Cesium carbonate → HCID 118079449, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-(4-(benzo[d]oxazol-2-yl)-6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)(cyclopropyl)methanone (0.019 g, 0.046 mmol), 1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.012 g, 0.051 mmol), tris(dibenzylideneacetone)dipalladium (2.1 mg, 2.3 μmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) (2.2 mg, 4.6 μmol) and cesium carbonate (0.045 g, 0.138 mmol) in dioxane (1.0 mL) and water (0.20 mL) was heated in the microwave at 100° C. for 1.5 h. The reaction mixture was filtered through Celite and concentrated to afford an orange oil. This material was purified via column chromatography on silica gel (Biotage 25 g column, gradient elution with 50-100% ethyl acetate-hexane) to afford (S)-(4-(benzo[d]oxazol-2-yl)-6-(1-cyclopropyl-1H-pyrazol-4-yl)-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)(cyclopropyl)methanone (0.014 g, 69%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.65-1.05 (m, 11 H), 1.85-2.02 (m, 1 H), 3.58-3.80 (m, 1H), 3.90-4.16 (m, 2 H), 5.02-5.18 (m, 1 H), 7.01-7.26 (m, 2 H), 7.31 (dd, J=8.21, 1.76 Hz, 1 H), 7.35-7.58 (m, 3 H), 7.79 (s, 1 H), 8.18 (s, 1 H), 8.36 (d, J=2.05 Hz, 1 H). MS (ESI, pos. ion) m/z 440 [M+H]+.

Provenance & Evidence