Water → HCID 58382162, compound

Participants

Reaction Steps

To a mixture of 1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (2.11 g, 5.81 mmol) in DMF (58 ml) was added NBS (1.03 g, 5.81 mmol). The mixture was stirred for about 2 h at rt. The mixture was poured into rapidly stirred water (˜300 mL). Saturated aqueous NaHCO3 (˜15 mL) was added and the mixture stirred for about 1 h. The solid was collected by filtration and washed with water (˜50 mL). The solid was dissolved in DCM (100 mL) and washed with saturated aqueous Na2CO3 (20 mL). The layers were separated and the aqueous layer was extracted with DCM (2×15 mL). The combined organic layers were washed with brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (80 g Silicycle™ column) eluting with 10% EtOAc in DCM to give 3-bromo-1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (1.62 g, 69%): LCMS (Table 2, Method b) Rt=2.52 min.; MS m/z: 404.96, 406 (M+H)+.

Provenance & Evidence