1,2-Dichloroethane → HCID 68183033, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-4-ol (745.8 mg, 2.10 mmol) in 1,2-dichloroethane (11.0 mL, 140 mmol) were added triethylsilane (3.35 mL, 20.9 mmol) and trifluoromethanesulfonic acid (0.927 mL, 10.5 mmol) and the resulting reddish solution was heated at 100° C. for 16 hr. The reaction mixture was allowed to cool to rt then was neutralized to pH 7 by the addition of a saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The organic layers were combined, washed with brine, 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 white foam (587.4 mg, 95% yield). LCMS: (FA) ES+ , 354. 1H NMR (400 MHz, DMSO-d6) δ: 8.45-8.49 (dd, J=1.5 Hz, J=4.7 Hz, 2H), 7.36-7.44 (m, 4H), 7.16-7.20 (dd, J=8.2 Hz, 2H), 7.10-7.12 (br s, 1H), 4.28-4.33 (m, 1H), 2.75-3.0 (m, 2H), 2.10-2.20 (m, 1H), 1.88-1.95 (m, 1H), 1.60-1.80 (m, 4H).

Provenance & Evidence