Phenol → HCID 11818359, compound

HRID 1677805Notes

Reaction equation

HRID 1677805 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14](=[N+]=[N-])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)=[O:5])[CH3:2].[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[O:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 996PhenolHCID 6577053H-Indole-2-carboxylic acid, 3-diazo-, ethyl ester

Product 1

HCID 11818359HCID 11818359, compoundYield 78%

Procedure

React 3-diazo-3H-indole-2-carboxylic acid ethyl ester, 5, (300 mg, 1.38 mmol) with phenol (5.0 equiv., 650 mg, 6.90 mmol) as described in General Synthetic Procedure VIII. Purify by flash chromatography to afford 3-phenoxy-1H-indole-2-carboxylic acid ethyl ester 6 (R1=phenyl, 303 mg, 78%) as a yellow solid. Hydrolyze the ester to the carboxylic acid 7 (R1=phenyl) using General Synthetic Procedure IX and then transform the carboxylic acid to the corresponding primary amide as described in General Synthetic Procedure V to afford the title compound Il as a light purple solid, tlc (silica gel) Rf=0.15.

Workup

  1. customPurify by flash chromatography

Sources & evidence

ORD record
ord-2e0385a511d24ea2ab5f71161eb83466
Source dataset
uspto-grants-2011_08
Patent number
US08008340B2

Reaction notes

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