反应 #2507862

反应方程式

triethylamine

tributyl(1-ethoxyvinyl)stannane

(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol

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title compound

收率 33.0%

(S)-1-(2-hydroxy-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-6-yl)ethanone

收率 33.0%

溶剂

dioxane

反应条件

后处理

1. 1
   其他An oven-dried scintillation vial equipped with a stirbar
2. 2
   其他purged with nitrogen for 5 min
3. 3
   其他The reaction was quenched with 1 N KHSO4
4. 4
   workup.ADDITIONThe mixture was then diluted with EtOAc
5. 5
   洗涤washed twice with NaHCO3 and once with brine
6. 6
   干燥The organic layer was dried over sodium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo

实验过程

An oven-dried scintillation vial equipped with a stirbar was charged with (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol (1.0 equiv), and (Ph3P)4Pd (0.07 equiv). The bottle was covered with a sheet of Parafilm and purged with nitrogen for 5 min, and anhydrous dioxane (13 volume equivalents), triethylamine (3.0 equiv), and tributyl(1-ethoxyvinyl)stannane (1.5 equiv) were added by syringe. The resulting mixture was heated to 80° C. overnight. The reaction was quenched with 1 N KHSO4 and stirred for 30 min. The mixture was then diluted with EtOAc, washed twice with NaHCO3 and once with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Biotage MPLC 10%-66% EtOAc/Hexanes) provided the title compound (33%) as a white solid. LCMS m/z (APCI)=283.1 (M+H).

来源