Allyl bromide → Methyl 8-chloro-3-(prop-2-en-1-yl)imidazo[1,2-a]pyrazine-2-carboxylate

Participants

Reaction Steps

To a suspension of methyl 3-bromo-8-chloroimidazo[1,2-a]pyrazine-2-carboxylate (250 mg, 0.861 mmol) in THF (8.6 mL) cooled to −40 C was added isopropylmagnesium chloride (0.99 mL, 1.29 mmol) dropwise. After 1 h stirring, copper cyanide (7.7 mg, 0.09 mmol) and allyl bromide (0.15 mL, 1.7 mmol) were added and the mixture was warmed to r.t. After 1 h, the reaction was poured into brine. The organic layer was separated, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified on silica (gradient elution, 0-80% EtOAc/hexanes) to yield the title product (48 mg). HRMS (ESI) calc (M+H)+=252.0534. found 252.0539.

Provenance & Evidence