Trimethylsilyl cyanide → HCID 59517233, compound

Participants

Reaction Steps

To 20 ml of a THF solution containing 1.9 g of 2-fluoro-4,5-dimethoxybenzaldehyde, 1.47 g of 4-amino-3-fluorobenzonitrile [CAS No. 63069-50-1], 6 g of MS3A, 640 mg of Yb(OTf)3, and 4 ml of trimethylsilyl cyanide were added under a nitrogen atmosphere. The resulting mixture was stirred at room temperature overnight and then filtered through celite. The filtrate was concentrated under reduced pressure, and ethyl acetate and water were added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane) and then filtered through NH silica gel to give the title compound (1.0 g) as a light yellow solid.

Provenance & Evidence