Methanol → 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionitrile

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Reaction Steps

To a solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (50 mg, 0.17 mmol) in dry DMF (1.0 mL) are added acrylonitrile (0.012 mL, 0.19 mmol) and 40% benzyltrimethyl ammonium hydroxide in MeOH (0.008 mL, 0.017 mmol). The resulting mixture is stirred at room temperature for 2 hr and then Sat. NH4Cl (2 mL) is added along with water (30 mL). Then the mixture is extracted with EtOAc (3×30 mL). The organic layers are combined, dried over MgSO4 and concentrated to give crude product. Purification by flash column chromatography affords 58 mg (98%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionitrile.

Provenance & Evidence