Reaktion #1904219

Reaktionsgleichung

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

(Z)-prop-1-enyl boronic acid

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title compound

Ausbeute 63.0%

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

Ausbeute 63.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA scintillation vial equipped with a stirbar
2. 2
   SonstigeThe vial was fitted with a septum-lined
3. 3
   Sonstigecap
4. 4
   Sonstigepurged with nitrogen for 5-10 min
5. 5
   workup.ADDITIONTo this mixture was added dioxane (16.6 volume equivalents)
6. 6
   Sonstigedegassed 2 N K2CO3 (4.2 volume equivalents) by syringe
7. 7
   TemperaturThe mixture was cooled to room temperature
8. 8
   workup.ADDITIONdiluted with EtOAc
9. 9
   Waschenwashed with twice with saturated aq. NaHCO3
10. 10
    TrocknenThe organic layer was dried over sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated in vacuo

Vorschrift

A 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), (Z)-prop-1-enyl boronic acid (2.0 equiv) and (DPPF)PdCl2 (0.10 equiv). The vial was fitted with a septum-lined cap and purged with nitrogen for 5-10 min. To this mixture was added dioxane (16.6 volume equivalents) and degassed 2 N K2CO3 (4.2 volume equivalents) by syringe. The resulting mixture was heated to 90° C. overnight. The mixture was cooled to room temperature, diluted with EtOAc, washed with twice with saturated aq. NaHCO3, and once with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Biotage MPLC 5%-40% EtOAc/Hexanes) provided the title compound (63%) as an off-white foam. LCMS m/z (APCI)=281.1 (M+H).

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