Dichloromethane → HCID 68183156, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube were added 2-bromo-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one (2.15 g, 8.77 mmol), 1,4-dioxane (54.8 mL, 702 mmol), pyridine-4-boronic acid (1.40 g, 11.4 mmol), cesium carbonate (8.50 g, 26.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (380 mg, 0.460 mmol) and water (7.90 mL, 439 mmol). The tube was sealed and the mixture was heated at 110° C. for 16 hr. The reaction mixture was allowed to cool to rt then diluted with ethyl acetate (15 mL) and water (10 mL) and transferred to a separatory funnel. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with brine (10 mL) then dried over anhydrous MgSO4. Insoluble materials were removed by filtration, the filtrate was 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 foam (1.44 g, 68% yield). LCMS: (FA) ES+ , 244. 1H NMR (300 MHz, DMSO-d6) δ: 8.55-8.57 (dd, J=1.7 Hz, J=4.9 Hz, 2H), 7.91-7.92 (br s, 1H), 7.62-7.64 (dd, J=1.5 Hz, J=4.9 Hz, 2H), 3.15-3.20 (m, 2H), 2.69-2.73 (m, 2H), 1.80-1.90 (m, 4H).

Provenance & Evidence