Cesium carbonate → HCID 136611525, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (E)-1-(1-(3-bromothiophen-2-yl)ethylidene)-2-(diphenylmethylene)hydrazine (12.5 g, 32.6 mmol, including its Z isomer) and (diphenylmethylene)hydrazine (7.68 g, 39.1 mmol) in toluene (25 mL) was added palladium(II) acetate (0.385 g, 6.52 mmol), 1,1′-bis(diphenylphosphino)ferrocene (1.808 g, 3.26 mmol) and Cs2CO3 (21.25 g, 65.2 mmol). The reaction mixture was heated at 80° C. for 14 hours. The mixture was subsequently diluted with toluene (25 mL) and filtered to remove solids. The filtrate was evaporated and chromatographed using a gradient of 0-100% hexane and EtOAc. The pure product fractions were combined and evaporated to give the title compound (12.5 g, 77%). ESI-MS m/z [M+H]+ calc'd for C32H26N4S, 499. found, 499.

Provenance & Evidence