Ethanol → HCID 21995927, compound

Participants

Reaction Conditions

Reaction Steps

In toluene (15 ml), ethanol (1.5 ml) and water (1.5 ml) were suspended 3-chloro-4-(3-ethoxypropoxy)phenyl borate (194 mg), 7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (300 mg) and potassium carbonate (208 mg). Under argon atmosphere, the suspension was stirred for 30 minutes, and to the mixture was added tetrakistriphenylphosphinepalladium (47 mg). Under argon atmosphere, the mixture was heated at 100° C. for 8 hours and cooled. To the mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate:ethano=18:1) and recrystallized from ethanol (23 ml) to give colorless crystals of 7-[3-chloro-4-(3-ethoxypropoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 131) (229 mg).

Provenance & Evidence