1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol → 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

HRID 1821867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821867
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH:10]([OH:12])[CH3:11]>C1COCC1.[O-2].[O-2].[Mn+4]>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=[O:12])[CH3:11]

Komponenten

4

Edukt 1

HCID 578934541-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol

Produkt 1

HCID 552679001-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol (Example 68) (0.65 g, 4.0 mmol) in THF (80 mL) was added manganese dioxide (4.18 g, 48 mmol). After stirring 2 h at room temperature, TLC analysis indicated that the reaction was completed. The reaction mixture was filtered through diatomaceous earth and rinsed with EtOAc. The filtrate was concentrated and triturated with Et2O to provide 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone as an off-white solid: mp 236-242° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.63 (3H, s), 7.34 (1H, s), 7.70-7.73 (1H, m), 8.13 (1H, d, J=5.7 Hz), 8.80 (1H, s); ESI MS m/z 161 [C9H8N2O+H]+; HPLC (Method A) 92.7% (AUC), tR=7.75 min.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washrinsed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customtriturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-82c0c50ccd6e4d9a894121c27b5cd972
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

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