2-Chloro-1,4-benzoquinone → 1-(4-tert-Butylphenyl)-6-chloro-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester

HRID 420944Notes

Reaction equation

HRID 420944 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[C:6]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[Cl:25][C:26]1[C:27](=[O:33])[CH:28]=[CH:29][C:30](=O)[CH:31]=1>>[CH2:1]([O:3][C:4]([C:5]1[C:29]2[C:30](=[CH:31][C:26]([Cl:25])=[C:27]([OH:33])[CH:28]=2)[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:16][CH:15]=2)[C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:24])[CH3:2]

Participants

3

Reactant 2

HCID 696712-Chloro-1,4-benzoquinoneHCID 666577413-(4-tert-Butylphenylamino)pent-2-enedioic acid diethyl ester

Product 1

HCID 666578111-(4-tert-Butylphenyl)-6-chloro-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester

Procedure

The sub-title compound was prepared in accordance with step (b) Example 1 from 3-(4-tert-butylphenylamino)pent-2-enedioic acid diethyl ester (6.2 g, 18.6 mmol, see step (a) above) and 2-chloro-1,4-benzoquinone (3.1 g, 22 mmol). Yield 266 mg (3%).

Sources & evidence

ORD record
ord-c2db75e89238476397aaff27ed6cf937
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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