Reaktion #1106895

Reaktionsgleichung

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

N-methylpyrrolidone

triethyl amine

(E)-tributyl(prop-1-enyl)stannane

→

title compound

Ausbeute 54.0%

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

Ausbeute 54.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA thick-walled microwave bottle equipped with a stirbar
2. 2
   Sonstigepurged with nitrogen for 5 min
3. 3
   SonstigeThe resulting mixture was immediately fitted with a septum
4. 4
   Sonstigecap
5. 5
   Waschenwashed four times with saturated aq. NaHCO3
6. 6
   TrocknenThe organic layer was dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A thick-walled microwave bottle 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 (0.12 equiv). The bottle was covered with a sheet of Parafilm and purged with nitrogen for 5 min, and N-methylpyrrolidone (14 volume equivalents), triethyl amine (2.0 equiv), and (E)-tributyl(prop-1-enyl)stannane (3.0 equiv) were added by syringe. The resulting mixture was immediately fitted with a septum and cap and heated to 120° C. in a microwave for 20 min. The reaction was then diluted with EtOAc, washed four times with saturated aq. NaHCO3 and once with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Reverse-phase preparative HPLC provided the title compound (54%) as a foam. LCMS m/z (APCI)=281.1 (M+H).

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