Imidazole → HCID 70113495, compound

Participants

Reaction Steps

To a suspension of the product from step (vii) (1.5 g) in dichloromethane (20 ml) was added a solution of boron tribromide (1M in dichloromethane) (6 ml). The mixture was stirred at room temperature for 2 hours. A further 10 ml of boron tribromide solution was added and the mixture was stirred for 2 hours before quenching with water. The pH was adjusted to 7 with sodium bicarbonate solution and the aqueous solution extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated under reduced pressure to give a brown solid. The solid was dissolved in N,N-dimethylformamide (20 ml) and treated with imidazole (0.68 g) followed by tert-butyldimethylsilyl chloride (0.68 g). The mixture was stirred overnight then partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and evaporated under reduced pressure. Purification was by precipitation with methanol/dichloromethane/isohexane.

Provenance & Evidence