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

HRID 1529636Notes

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]>>[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

Reactant 2

HCID 12183Ethyl iodoacetate

HCID 785026-Nitro-1H-indole

Product 1

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

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%).

Workup

customOverall yield (24%)

Sources & evidence

ORD record: ord-dd8632bca5ca4433b8dab4ee4df44a52
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090619B2

Reaction notes

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