(3-Chlorophenyl)boronic acid → 5-(3-Chlorophenoxy)-1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-indole-3-carboxylic acid ethyl ester

HRID 420953Notes

Reaction equation

HRID 420953 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2].[Cl:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:38]3[CH:37]=[CH:36][CH:35]=[C:34]([Cl:33])[CH:39]=3)[CH:13]=2)[N:8]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 666576271-(4-Diethylaminophenyl)-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester

Product 1

HCID 666575815-(3-Chlorophenoxy)-1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-indole-3-carboxylic acid ethyl ester

Procedure

The sub-title compound was prepared in accordance with step (c) Example 1 from 1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester (150 mg, 0.34 mmol, see step (b) Example 1) and 3-chlorophenylboronic acid (110 mg, 0.68 mmol). Yield 100 mg (53%).

Sources & evidence

ORD record
ord-d7a71189128f43dd86152273be8c2ee6
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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