4-bromo-N-tert-butylbenzamide → HCID 11609336, compound

Participants

Reaction Conditions

Reaction Steps

11.6 ml of n-butyllithium (1.6M in hexane) are added dropwise to a solution of 4.250 mmol of 4-bromo-N-tert-butylbenzamide in 200 ml of tetrahydrofuran at −78° C. After 90 minutes, a solution of 6.00 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [51907-18-7] in 4 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred at −78° C. for 1 hour and at room temperature for 2 hours and then quenched with saturated aqueous ammonium chloride solution. The organic phase is separated off and the aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are dried with sodium sulphate and evaporated. The title compound is obtained as a yellow solid from the residue by flash chromatography (SiO2 60F). Rf=0.16 (dichlormethane:methanol=95:5), Rt=4.96.

Provenance & Evidence