Ethyl iodoacetate → (6-Amino-1H-indol-3-yl)-acetic acid ethyl ester

HRID 73937

Reaction equation

HRID 73937 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[CH2:13]([O:15][C:16](=[O:19])[CH2:17]I)[CH3:14]>CC#N>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][C:8]1[C:7]2[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=2)[NH:10][CH:9]=1)[CH3:14]

Participants

4

Reactant 2

HCID 12183Ethyl iodoacetateHCID 785026-Nitro-1H-indole

Product 1

HCID 66675483(6-Amino-1H-indol-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(6-Amino-1H-indol-3-yl)-acetic acid ethyl ester (B-17) was synthesized following the general scheme above starting from 6-nitroindole and iodo-acetic acid ethyl ester. Overall yield (24%). HPLC ret. time 0.95 min, 10-99% CH3CN, 5 min run; ESI-MS 219.2 m/z (MH+).

Workup

  1. customOverall yield (24%)

Sources & evidence

ORD record
ord-ed116ac2db13497eaec502a4321fada4
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Linked notes

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