Water → (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)-6-(2H-tetrazol-5-yl)quinoxaline

HRID 1405309

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]#[N:25])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.O.[N:27]([Na])=[N+:28]=[N-:29]>CS(C)=O.Br[Zn]Br>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]4[N:27]=[N:28][NH:29][N:25]=4)[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

To a solution of (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carbonitrile (100 mg, 0.30 mmol) in DMSO (10 mL) was added dibromozinc (33.8 mg, 0.15 mmol), water (10 mL), azidosodium (48.8 mg, 0.75 mmol) and water (5 mL). The resulting solution was stirred for 1 days at 125° C. and then quenched by the addition of water (100 mL), extracted with dichloromethane (3×30 mL). The organic layers were combined and dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (2% dichloromethane in methanol) to afford (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)-6-(2H-tetrazol-5-yl)quinoxaline as a yellow solid (70.9 mg, 63%).

Aufarbeitung

customquenched by the addition of water (100 mL)
extractionextracted with dichloromethane (3×30 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto give a residue, which
customwas purified via silica gel column chromatography (2% dichloromethane in methanol)

Quellen und Nachweise

ORD-Eintrag: ord-c9bee96bffa14a1fb7fe9c4edfb7a55f
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08916561B2

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