Ethanol → HCID 21995686, compound

Participants

Reaction Steps

In toluene (10 ml), ethanol (1 ml) and water (1 ml) were suspended 4-(2-ethoxyethoxy)-3-methylphenyl borate (119 mg), 7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (212 mg) and potassium carbonate (147 mg), and the suspension was stirred under argon atmosphere for 30 minutes. To the mixture was added tetrakistriphenylphosphinepalladium (33 mg), and the mixture was stirred under argon atmosphere at 100° C. for 8 hours and cooled. To the mixture was added saturated brine, and the mixture was extracted with ethyl acetate (twice). 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:methanol=7:1) and recrystallized from ethanol (22.5 ml) to give colorless crystals of 7-[4-(2-ethoxyethoxy)-3-methyl-phenyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 129) (131 mg).

Provenance & Evidence