Dimethylacetamide → HCID 58381980, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-6-(4-methoxyphenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (1.5 g, 3.5 mmol, prepared using A from 3,5-dibromopyrazin-2-amine with 1-ethynyl-4-methoxybenzene, B and C) in THF (20 mL) was cooled to about −75° C. then n-BuLi (1.44 mL, 3.45 mmol) was added dropwise keeping the temperature below −70° C. After about 5 min DMA (1.30 mL, 13.8 mmol) was added keeping the temperature below about −65° C. The mixture was stirred for about 30 min at about −75° C. then allowed to warm slowly to about 0° C. AcOH (˜0.5 mL) was added then the mixture was diluted with water (40 mL), saturated aqueous Na2CO3 (20 mL) and EtOAc (40 mL). The layers were separated then the organic layer was washed with brine (20 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on an 80 g silica column with 85:15 DCM/EtOAc as an eluent to give 1-(6-(4-methoxyphenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)ethanone (1.04 g, 76%): LC/MS (Table 2, Method a) Rt=3.42 min; MS m/z 398 (M+H)+.

Provenance & Evidence