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

HRID 646071Notes

Reaction equation

HRID 646071 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.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[CH:24]1>>[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:24]1[NH:23][C:31]2[C:26]([C:25]=1[CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[CH:27][CH:28]=[CH:29][CH:30]=2

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 12932197N-((1H-indol-3-yl)methyl)acetamideHCID 685819552-Methyl-2-p-tolyl-cyclobutane-1,3-dione

Product 1

HCID 59264915N-{2-[(2-Hydroxy-3-methyl-4-oxo-3-p-tolyl-cyclobut-1-enyl)-phenyl-methyl]-1H-indol-3-ylmethyl}-acetamide

Procedure

Using general procedure C, 2-methyl-2-p-tolyl-cyclobutane-1,3-dione (from Example 4.1) was reacted with benzaldehyde and N-(1H-indol-3-ylmethyl)-acetamide (Lit. 6) to give the title compound as an off-white solid. MS: 463.4 ([M−H]−).

Sources & evidence

ORD record
ord-5efaf043d70d4a05bb95625aedb7ebd5
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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