Sodium hydride → (E)-5-[2-(4-chlorophenylthio)styryl]-8-(2-furyl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepine dihydrochloride

Participants

Reaction Conditions

Reaction Steps

To 123 mg (0.32 mmol) of (8-bromo-1-methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester (prepared as described in Example 41) in 2 ml of dioxane was added 135 mg (0.38 mmol) of 2-(tributylstannyl)furan, followed by 11.1 mg (0.016 mmol) of palladium (II) bis-triphenylphosphine-dichloride. The mixture was heated at 80° C. for 18 hours. To the mixture at ambient temperature was added 55 mg (1.37 mmol) of sodium hydride (60% dispersion in mineral oil). After 5 minutes 82 mg (0.33 mmol) of 2-(4-chlorophenylthio)benzaldehyde was added and the mixture was stirred for 18 hours. The solvent was removed and the product was purified by column chromatography eluting with 24-40% acetone/petroleum ether (40-60° C.) and treated with 0.10 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated and the residue was dissolved from acetone/petroleum ether (40 60° C.). The solvent was removed and the residue was recrystallised from acetone/petroleum ether (40 60° C.) to give 63 mg of (E)-5-[2-(4-chlorophenylthio)styryl]-8-(2-furyl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepine dihydrochloride as dark red crystals; MS: m/e 471 (M+).

Provenance & Evidence