Indole → 3-(1H-Indol-3-yl)cyclopentanone

HRID 1072445Notes

Reaction equation

HRID 1072445 reaction equation
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=C2OCC1)N=CC=C3.CC1C=C(C)C=CC=1S([O-])(=O)=O.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28]1.C1(=O)CCC=C1>>[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH:13]2[CH2:12][CH2:7][C:6](=[O:1])[CH2:14]2)=[CH:28]1

Participants

4

Reactant 3

HCID 798IndoleHCID 135882-Cyclopenten-1-oneHCID 865941822,3-Dihydro-1,4-dioxino[2,3-f]-quinoline 2-methyltosylate

Product 1

HCID 113446533-(1H-Indol-3-yl)cyclopentanoneYield 44%

Procedure

This compound was prepared in similar manner as for Intermediate 14, using indole (2.34 g, 20 mmol) and 2-cyclopenten-1-one (2.0 mL, 24.0 mmol) to give 1.7 g (44%) of the desired product as a thick oil: MS (ESI) m/z 200 [M+H]+.

Sources & evidence

ORD record
ord-fca9e5eec5644e798319d02092bd952f
Source dataset
uspto-grants-2005_06
Patent number
US06911445B2

Reaction notes

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