Iodine → HCID 66734000, compound

Participants

Reaction Steps

A cooled (−30° C.) solution of 8-[2-(4-chloro-3,5-difluoro-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (1.790 g; 3.244 mmol) in anhydrous THF (90 ml) was treated dropwise with a solution of 1-Methylmagnesium bromide in THF (14.6 ml; 14.6 mmol; 4.5 eq.) until complete removal of the iodine substituent. The mixture was then quenched with water (10 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-chloro-3,5-difluoro-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow solid (1.150 g; 83%). LC-MS: tR=0.95 min.; [M+H]+=426.01 g/mol.

Provenance & Evidence