Triethylamine → HCID 68654609, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[(4-bromo-2-fluoro-phenyl)-cycloheptylidene-methyl]-phenol (175) (1.0 g, 2.66 mmol) in DMF (27 mL) was added ethyl acrylate (2.9 mL, 26.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.187 g, 0.266 mmol) and Et3N (2.2 mL, 15.99 mmol). The reaction mixture was heated at 100° C. for 20 h. The reaction mixture was cooled to room temperature and diluted with water (10 mL) and EtOAc (20 mL). The aqueous mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was loaded onto silica gel and purified by flash chromatography with a hexanes:EtOAc gradient (100:0 to 90:10) to give 0.85 g (81%) of the title compound 176 as an oil. 1H NMR (400 MHz, DMSO-d6): δ 1.22 (t, J=7.1 Hz, 3 H), 1.48-1.51 (m, 8 H), 2.07-2.10 (m, 2 H), 2.25 (s, 2 H), 4.13-4.18 (m, 2 H), 6.61-6.66 (m, 3 H), 6.92 (d, J=8.6 Hz, 2 H), 7.20 (t, J=7.8 Hz, 1 H), 7.47 (d, J=6.6 Hz, 1 H), 7.56-7.60 (m, 2 H), 9.32 (s, 1 H).

Provenance & Evidence