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

HRID 606778Notes

Reaction equation

HRID 606778 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-fa6e72324e3b4cecbd6fd28ebcef2b6b
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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