4-Methoxyphenol → HCID 86613184, compound

HRID 1677806Notes

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].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([O:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 90154-Methoxyphenol

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

Product 1

HCID 86613184HCID 86613184, compoundYield 51%

Procedure

React 3-diazo-3H-indole-2-carboxylic acid ethyl ester, 5, (231 mg, 1.10 mmol) with 4-methoxyphenol (1.4 equiv., 186 mg, 1.5 mmol) as described in General Synthetic Procedure VIII to afford 3-(4-methoxyphenoxy-1H-indole-2-carboxylic acid ethyl ester 6 (R1=4-methoxyphenyl, 169 mg, 51%) as an ivory-colored solid. Hydrolyze the ester to the carboxylic acid 7 (R1=4-methoxyphenyl) 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 Im as a colorless oil, tlc (silica gel) Rf=0.10.

Sources & evidence

ORD record: ord-4a24e7425f9c4fe88027d4e80c1002a1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008340B2

Reaction notes

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