Dimethylformamide → HCID 86641104, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(5-(5-(4-bromophenoxy)-3-(2-chlorophenylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (500 mg, 0.741 mmol) was dissolved in THF (7 mL) and cooled to −78° C. Methyllithium (556 μL, 0.889 mmol) was added and the reaction was stirred for 5 minutes. Butyllithium (356 μL, 0.889 mmol) was added and the reaction was stirred for 5 minutes. N,N-dimethylformamide (115 μL, 1.48 mmol) was added and the reaction was slowly warmed to ambient temperature. The reaction was poured into NH4Cl, extracted with EtOAc, concentrated and purified on silica gel (5 to 10% EtOAc in hexanes) to afford tert-butyl 4-(5-(3-(2-chlorophenylthio)-5-(4-formylphenoxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (183 mg, 0.293 mmol, 39.6% yield) as a white solid.

Provenance & Evidence