Trifluoroacetic acid → HCID 178509560, compound

Participants

Reaction Steps

2′-[Hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-biphenyl-4-carbonitrile (Intermediate D2) (2.4 g, 4.6 mmol) in CH2Cl2 (100 mL) was cooled to 0° C. and treated with triethyl silane, Et3SiH (7.4 mL, 46 mmol) (commercially available from Aldrich) followed by trifluoroacetic acid, TFA (10.7 mL, 140 mmol) dropwise. After several minutes the cooling bath was removed and the mixture was stirred at rt for an additional 12 h. The reaction was quenched with solid NaHCO3 followed by aqueous workup. The layers were separated and the organic layers were combined and dried over Na2SO4. The mixture was filtered and concentrated to dryness. The residue was purified by chromatography on silica gel with 3% NH3-MeOH: CH2Cl2 to give the product 2′-(1H-imidazol-4-ylmethyl)-biphenyl-4-carbonitrile (Intermediate D3), 0.74 mg, 62% yield.

Provenance & Evidence