Sodium hydride → (3RS)-1-(benzofuran-2-yl)methyl-2,3-dihydro-5-(2-fluorophenyl)-3-phthalimido-1H-1,4-benzodiazepin-2-one

Participants

Reaction Steps

To a suspension of sodium hydride (0.185 g of a 60% dispersion in mineral oil) in dry N,N-dimethylformamide (5 ml) was added (3RS)-2,3-dihydro-5-(2-fluorophenyl)-3-phtalimido-1H-1,4-benzodiazepin-2-one (1.700 g) under stirring at cooling in an ice-bath. The mixture was stirred under the same condition for 1 hour and then at room temperature for 1.5 hours. To the mixture was added dropwise a solution of 2-bromomethylbenzofuran (1.076 g) in N,N-dimethylformamide (5 ml) under cooling in an ice-bath. After completion of the addition, the mixture was allowed to stand to room temperature overnight. The reaction mixture was concentrated in vacuo. The residue was treated with ethyl acetate and water. The organic layer was washed with water and a brine, and dried over magnesium sulfate. Removal of the solvent gave (3RS)-1-(benzofuran-2-yl)methyl-2,3-dihydro-5-(2-fluorophenyl)-3-phthalimido-1H-1,4-benzodiazepin-2-one (1.018 g) which was used in a following reaction step without further purification.

Provenance & Evidence