4-Methoxy-7-(3-hydroxy-1-butyn-1-yl)-6-azaindole → 4-Methoxy-7-(3-oxo-1-butyn-1-yl)-6-azaindole

HRID 1394456Notes

Reaction equation

HRID 1394456 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[N:10][C:9]([C:12]#[C:13][CH:14]([OH:16])[CH3:15])=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2>C(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:11]=[N:10][C:9]([C:12]#[C:13][C:14](=[O:16])[CH3:15])=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2

Participants

4

Reactant 1

HCID 596816704-Methoxy-7-(3-hydroxy-1-butyn-1-yl)-6-azaindole

Product 1

HCID 596817084-Methoxy-7-(3-oxo-1-butyn-1-yl)-6-azaindoleYield 80.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-7-(3-hydroxy-1-butyn-1-yl)-6-azaindole (0.200 g, 0.88 mmol) in CH2Cl2 (25 mL) was added activated MnO2 (1.72 g) and the reaction mixture was stirred for 12 h. The mixture was then filtered through Celite and the filtrate was concentrated to afford the title compound (0.152 g, 80%) as a light brown solid:

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0b4e286beea54382ab0a6c1885ad5a43
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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