Iodine → HCID 66734093, compound

Participants

Reaction Steps

A cooled (−30° C.) solution of 8-[2-(4-bromo-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (2.200 g; 3.927 mmol) in anhydrous THF (90 ml) was treated dropwise with a solution of 1-Methylmagnesium bromide in THF (10.25 ml; 10.25 mmol; 2.6 eq.) until complete removal of the iodine substituent. The mixture was then quenched with water (5 ml), diluted with ether (100 ml), and was allowed to warm-up to rt. This solution was washed with brine (2×150 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=15/1) to give the pure product 8-[2-(4-bromo-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (1.570 g; 92%). LC-MS: tR=0.93 min.; [M+H]+=435.98 g/mol.

Provenance & Evidence