Allyl bromide → HCID 58382309, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.500 g, 0.964 mmol, Preparation #5) in THF (6 mL) was cooled to about −75° C. then the n-BuLi (2.4 M in hexanes, 0.482 mL, 1.16 mmol) was added dropwise. After about 10 min CuCN (0.009 g, 0.010 mmol) was added followed by allyl bromide (0.250 mL, 2.89 mmol). The mixture was stirred at about −70° C. for about 30 min warmed to about −40° C. the mixture was treated with about 2 mL of saturated aqueous NaHCO3 then warmed to rt. The mixture was diluted with EtOAc (20 mL) and water (10 mL). The layers were separated and the aqueous layer extracted with EtOAc (10 mL). The combined organics were washed with brine (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified on a 10 gram silica column with 9:1 DCM/EtOAc as an eluent to give 2-allyl-7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.323 g, 70%): LC/MS (Table 2, Method b) Rt=3.53 min; MS m/z 480 (M+H)+.

Provenance & Evidence