Cesium carbonate → HCID 87113365, compound

Participants

Reaction Steps

A mixture of Example 26D (291 mg, 0.544 mmol), benzophenone imine (0.18 mL, 1.1 mmol), cesium carbonate (390 mg, 1.20 mmol), tris(dibenzylideneacetone)dipalladium(0) (14 mg, 0.015 mmol), and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (22 mg, 0.035 mmol) in dimethoxyethane (2.2 mL) was heated at 150° C. for 25 minutes in a microwave reactor. The mixture was cooled to room temperature, and the solution was pipetted away from the residual solid and concentrated. Chromatography of the resulting residue on silica gel (1 to 5% ethyl acetate-hexane, eluant) afforded 263 mg (85% yield) of the title compound as a sticky yellow oil/foam. 1H NMR (300 MHz, DMSO-d6) δ 7.19-7.74 (m, 18H), 6.92 (m, 2H), 6.77 (m, 1H), 6.60 (m, 1H), 6.18 (m, 1H), 4.12 (m, 1H), 2.53-2.62 (m, 3H), 2.38 (m, 1H), 1.84 (m, 1H), 1.72 (m, 1H), 0.99 (s, 9H). MS (DCI+) m/z 566 (M+H)+.

Provenance & Evidence