Benzyl Alcohol → HCID 11185523, compound

HRID 1677807Notes

Reaction equation

HRID 1677807 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].[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 244Benzyl AlcoholHCID 6577053H-Indole-2-carboxylic acid, 3-diazo-, ethyl ester

Product 1

HCID 11185523HCID 11185523, compound

Procedure

React 3-diazo-3H-indole-2-carboxylic acid ethyl ester, 5, (305 mg, 1.4 mmol) with benzyl alcohol (5.0 equiv., 0.73 mL, 7.05 mmol) as described in General Synthetic Procedure VIII to afford 3-benzyloxy-1H-indole-2-carboxylic acid ethyl ester 6 (R1=benzyl) as a white solid [MS obs=296 (M+1)]. Hydrolyze the ester to the carboxylic acid 7 (R1=benzyl) 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 Iu as a tan solid (115 mg), tlc (silica gel) Rf=0.1.

Sources & evidence

ORD record
ord-4e3935f1180b44e4b6df287e516c7c8f
Source dataset
uspto-grants-2011_08
Patent number
US08008340B2

Reaction notes

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