1,2-Dichloroethane → HCID 68183344, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta thiophene-4-ol (500.0 mg, 1.405 mmol) in 1,2-dichloroethane (6.0 mL, 76 mmol) trifluoroacetic acid (1.082 mL, 14.05 mmol) was added at 0° C., and the resulting brownish solution was heated at 60° C. for 16 hr. The reaction mixture was allowed to cool to rt, the solvent was evaporated, saturated NaHCO3 (5 mL) and ethyl acetate (5 mL) were added, and the mixture was stirred for 30 min, the organic layer was separated, the aqueous layer was extracted with ethyl acetate (3×5 mL), the combined organic layers were dried over MgSO4, filtered, concentrated and the obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/DCM) to give the title compound as a yellow solid (428.7 mg, 91.2% yield). LCMS: (FA) ES+ , 338/340. 1H NMR (300 MHz, DMSO) E. 8.64 (d, J=6.7 Hz, 2H), 7.92 (d, J=6.6 Hz, 2H), 7.63 (s, 1H), 7.47-7.37 (m, 2H), 7.37-7.21 (m, 2H), 6.49 (t, J=6.5 Hz, 1H), 2.91 (t, J=6.4 Hz, 2H), 2.31-2.07 (m, 4H).

Provenance & Evidence