Benzaldehyde → N-{2-[(2-Hydroxy-3-methyl-4-oxo-3-p-tolyl-cyclobut-1-enyl)-phenyl-methyl]-6-methyl-1H-indol-3-ylmethyl}-N-methyl-formamide

HRID 646077Notes

Reaction equation

HRID 646077 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[CH2:4][C:3]1=[O:7].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:23][N:24]([CH2:27][C:28]1[C:36]2[C:31](=[CH:32][C:33]([CH3:37])=[CH:34][CH:35]=2)[NH:30][CH:29]=1)[CH:25]=[O:26]>>[OH:7][C:3]1[C:2]([CH3:1])([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[C:4]=1[CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:29]1[NH:30][C:31]2[C:36]([C:28]=1[CH2:27][N:24]([CH3:23])[CH:25]=[O:26])=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=2

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 685819552-Methyl-2-p-tolyl-cyclobutane-1,3-dioneHCID 86619843N-methyl-N-(6-methyl-1H-indol-3-ylmethyl)-formamide

Product 1

HCID 25050876N-{2-[(2-Hydroxy-3-methyl-4-oxo-3-p-tolyl-cyclobut-1-enyl)-phenyl-methyl]-6-methyl-1H-indol-3-ylmethyl}-N-methyl-formamide

Procedure

Using general procedure C, 2-methyl-2-p-tolyl-cyclobutane-1,3-dione (from Example 4.1) was reacted with benzaldehyde and N-methyl-N-(6-methyl-1H-indol-3-ylmethyl)-formamide to give the title compound as a red solid. MS: 476.6 ([M−H]−).

Sources & evidence

ORD record
ord-989f399f45ba44b8b6e7d997b8d8e650
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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