Cesium carbonate → HCID 69813110, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of (A3) in DMF (0.1 M), Cs2CO3 (1.1 eq.), tris(dibenzenzylideneacetone)dipalladium(0) (0.05 eq.), tri-t-butylphosphonium tetrafluoroborate (0.15 eq.) and tributyl[(Z)-2-ethoxyvinyl]stannane (2.0 eq.) were added at RT and the reaction mixture was heated to 70° C. for 12 h. After cooling down, the solvent was reduced in vacuo and the residue partioned between sat. aq. NaHCO3 and DCM. The aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave a residue which was purified by flash column on silica using a gradient of EtOAc/Petroleum ether from 30:70 to 50:50 to yield (74%) the title compound as a yellow oil, it is a mixture of regioisomers (cis/trans=4:1). 1H NMR (300 MHz, CDCl3, 300K) δ 8.10 (2H, d, J=8.3 Hz), 7.90 (1H, d, J=8.7 Hz), 7.70 (2H, d, J=8.3 Hz), 7.40 (1H, d, J=6.4 Hz), 7.35-7.25 (1H, m), 6.32 (1H, d, J=6.7 Hz), 5.65 (1H, d, J=6.4 Hz), 3.97 (3H, s), 3.74 (2H, q, J=7.0 Hz), 1.03 (3H, t, J=7.0 Hz). MS (ES+) C20H17N3O3 requires: 347, found: 348 (M+H)+.

Provenance & Evidence