Reacción #2507862

Ecuación de reacción

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

Rendimiento 33.0%

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

Rendimiento 33.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAn oven-dried scintillation vial equipped with a stirbar
2. 2
   Otropurged with nitrogen for 5 min
3. 3
   OtroThe reaction was quenched with 1 N KHSO4
4. 4
   workup.ADDITIONThe mixture was then diluted with EtOAc
5. 5
   Lavadowashed twice with NaHCO3 and once with brine
6. 6
   SecadoThe organic layer was dried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

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).

Fuente