Acetonitrile → HCID 11992473, compound

Participants

Reaction Steps

A suspension of [(4-Bromophenyl)(phenyl)methylene]cycloheptane (1) (0.50 g, 1.47 mmol), TEA (1.21 mL, 8.71 mmol), acrylamide (0.62 g, 8.73 mmol), Pd(OAc)2 (0.080 g, 0.36 mmol), P(o-tolyl)3) (0.19 g, 0.63 mmol) and CH3CN was stirred at reflux under N2. After 2 h heating was discontinued and the reaction diluted with EtOAc (50 mL) and water (50 mL). The mixture was filtered through a celite pad and the filtrate transferred to a separatory funnel. The organic fraction was washed with brine (50 mL), dried (MgSO4), filtered and concentrated to an amber oil. This oil was purified by column chromatography on silica gel (50 g) using a hexanes to 25% EtOAc:hexanes to 100% EtOAc gradient to afford a pale yellow solid. Trituration of the solid with EtOAc (25 mL) yielded 164 mg (33%) of the title compound (4) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 1.54 (s, 8H), 2.24 (br s, 4H), 6.55 (d, J=15.9 Hz, 1H), 7.07 (br, 1H), 7.14-7.20 (m, 7H), 7.25 (d, J=15.9 Hz, 1H), 7.49 (d, J=8.1 Hz, 2H), 7.50 (br, 1H). LRMS (APCI): m/z 332 (M+H)+. Anal. Calcd for C23H25NO.0.1H2O: C, 82.67; H, 7.63; N, 4.19. Found: C, 82.75; H, 7.56; N, 4.20.

Provenance & Evidence