Trifluoroacetic acid → HCID 90077325, compound

Participants

Reaction Conditions

Reaction Steps

Potassium hydrogen fluoride (0.697 g, 8.92 mmol) and N-(4-bromobenzylidene)-cyclopropanamine (2 g, 8.92 mmol) were dissolved in acetonitrile (17.85 ml) and cooled to 0° C. TFA (1.031 ml, 13.39 mmol) was added and the reaction was stirred for 5 min. Then (trifluoromethyl)trimethylsilane (2.64 ml, 17.85 mmol) was added and the reaction was allowed to stir at rt overnight. Saturated Na2CO3 was added to the reaction mixture and the reaction stirred 5 min, then diluted with water and EtOAc/Hexane (1:1). The aqueous phase was extracted with EtOAc (×2), and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 2% to 25% EtOAc:Hexane to give product. A second purification was performed on this product on a Biotage™ 100 g column by eluting with 2% to 25% EtOAc to provide the desired product. LC-MS: calculated for C11H11BrF3N 293.00 observed m/e: 294.15 (M+H)+ (Rt 1.23/2 min).

Provenance & Evidence