5-Ethyl-2-(1-hydroxy-ethyl)-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one → 2-Acetyl-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 1181577Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]3[N:12]=[C:13]([CH:15]([OH:17])[CH3:16])[NH:14][C:8]3=[CH:7][C:6]=2[C:5]([CH3:19])([CH3:18])[C:4]1=[O:20])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:15]([C:13]1[NH:14][C:8]2=[CH:7][C:6]3[C:5]([CH3:19])([CH3:18])[C:4](=[O:20])[N:3]([CH2:1][CH3:2])[C:11]=3[CH:10]=[C:9]2[N:12]=1)(=[O:17])[CH3:16]

Participants

Conditions

Temperature: 65 °C

Procedure

5-Ethyl-2-(1-hydroxy-ethyl)-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (13 g, 47.6 mmol) and manganese(IV)dioxide (16.54 g, 190 mmol) were suspended in chloroform (400 mL) and stirred at 65° C. for 16 h. The mixture was cooled, filtered over Celite and the filtrate concentrated in vacuo yielding 11.6 g (90%) of a beige solid.

Workup

temperatureThe mixture was cooled
filtrationfiltered over Celite
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-c7f86cc9f343413889f43923ba7ad516
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285569B2

Reaction notes

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