Indoline → 4-(2,3-Dihydro-1H-indol-1-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 585368Notes

Reaction equation

HRID 585368 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11](O)[CH2:10][C@@H:9]1[CH3:19])=[O:7].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1>>[N:25]1([CH:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([C:6](=[O:7])[C:5]3[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]([CH3:19])[CH2:10]2)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 10328IndolineHCID 69774154cis-1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

Product 1

HCID 223393374-(2,3-Dihydro-1H-indol-1-yl)-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolineYield 51.1%

Procedure

Starting with cis-1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol (400 mg, 1.22 mmol) prepared in Reference Example 1 and indoline (436 mg, 3.66 mmol), the same procedure as shown in Example 1 was repeated to give the titled compound (267 mg, yield: 51%) as a white crystal. (cis:trans=1:1.8)

Sources & evidence

ORD record
ord-2a2ba6d015aa43bd9d450e37407a073a
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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