Water → 2-(4-(N-Cyanomethyl-S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

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Reaction Steps

A mixture of 2-(4-(S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione (preparation 17b, 500 mg, 1.59 mmol) and 1,2-dimethoxyethane (2 mL) is added to a mixture of potassium hydride (30%, 260 mg, 1.95 mmol) in 1,2-dimethoxyethane (3 mL). The mixture is stirred for 15 min at room temperature and treated with tetraethylammonium bromide (10 mg, 0.05 mmol) and bromoacetonitrile (220 μL, 3.16 mmol). The mixture is heated at 110° C. over night and cooled to room temperature. Water is added, and the mixture is extracted twice with dichloromethane. The organic layer is concentrated under reduced pressure, and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:0 to 0:1). Yield: 155 mg (27% of theory). ESI mass spectrum: [M+H]+=354; r.t. HPLC: 0.47 min (X011_S03).

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