Sodium hydride → 7-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-2,3,5,6,7,11c-hexahydro-1H-pyrido[3',2':4,5]pyrrolo[2,3-g]indolizine

HRID 1497970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497970
[CH2:1]1[CH:16]2[N:4]([CH2:5][CH2:6][C:7]3[NH:8][C:9]4[N:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:15]=32)[CH2:3][CH2:2]1.[H-].[Na+].[O:19]1[CH2:21][CH:20]1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>CN(C=O)C>[N:25]1[CH:26]=[CH:27][C:22]([CH:20]([OH:19])[CH2:21][N:8]2[C:7]3[CH2:6][CH2:5][N:4]4[CH:16]([C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]2=3)[CH2:1][CH2:2][CH2:3]4)=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 109534834-(Oxiran-2-yl)pyridineHCID 670366062,3,4,5,6,10c-hexahydro-1H-3a,6,7-triaza-cyclopenta[c]fluorene

Produkt 1

HCID 584598877-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-2,3,5,6,7,11c-hexahydro-1H-pyrido[3',2':4,5]pyrrolo[2,3-g]indolizine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,3,4,5,6,10c-hexahydro-1H-3a,6,7-triaza-cyclopenta[c]fluorene (1 g, 4.6 mmol) in DMF (20 mL) were portion wise added NaH (60%, 0.552 g, 13.8 mmol) and 4-(oxiran-2-yl)pyridine (0.709 g, 5.6 mmol). The reaction mass was stirred at RT overnight. The progress of reaction was monitored by LCMS. The reaction mixture was quenched with ice cold water (300 mL) and extracted with EtOAc (3×100 mL). The combined organic layer was washed with water (10×100 mL), followed by brine (2×100 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography followed by reverse phase HPLC to yield the title compound;

Aufarbeitung

  1. customThe progress of reaction
  2. customThe reaction mixture was quenched with ice cold water (300 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic layer was washed with water (10×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-62e82c14a3694ac1ba300c3e16dc1717
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199996B2

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