4-Aminobenzonitrile → HCID 67504429, compound

Participants

Reaction Steps

After adding 18 g of 4-aminobenzonitrile, 50 g of MS3A, 6.65 g of Yb(OTf)3 and 28.6 ml of trimethylsilyl cyanide to a solution of 50.04 g of 2-fluoro-5-methoxy-3-triisopropylsilanyloxybenzaldehyde (Example 3b) in 300 ml of THF under a nitrogen atmosphere, the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained solid was suspended in ethyl acetate-heptane (1:2) and the solid was filtered to give 4-{[cyano-(2-fluoro-5-methoxy-3-triisopropylsilanyloxyphenyl)methyl]amino}benzonitrile (59.32 g).

Provenance & Evidence