Diisopropylethylamine → N-[2-(1,3-dimethylbutyl)phenyl]-2-iodothiophene-3-carboxamide

Participants

Reaction Steps

Under protective gas (argon), 0.56 ml (3.38 mmol) of N,N-diisopropylethylamine and 1.18 g (2.5 mmol) of bromotrispyrrolidinophosphonium hexafluorophosphate (PyBrop) are added to a solution of 516 mg (2.0 mmol) of 2-iodothiophene-3-carboxylic acid and 300 mg (1.7 mmol) of 2-(1,3-dimethylbutyl)phenylamine in 10 ml of acetonitrile. The reaction mixture is stirred at room temperature for 24 hours and, for work-up, added to water, extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure. Column chromatography (cyclohexane/ethyl acetate gradient) gives 150 mg (21% of theory) of N-[2-(1,3-dimethylbutyl)phenyl]-2-iodothiophene-3-carboxamide [log P (pH 2.3)=4.14].

Provenance & Evidence