Ethyl Bromide → 3-ethyl-1H-indol-6-amine

HRID 469970Notes

Reaction equation

HRID 469970 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](Br)[CH3:14]>CC#N>[CH2:13]([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 6332Ethyl BromideHCID 785026-Nitro-1H-indole

Product 1

HCID 451170143-ethyl-1H-indol-6-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Ethyl-1H-indol-6-ylamine (B-12) was synthesized following the general scheme above starting from 6-nitroindole and ethyl bromide. Overall yield (42%). HPLC ret. time 1.95 min, 10-99% CH3CN, 5 min run; ESI-MS 161.3 m/z (MH+).

Workup

  1. customOverall yield (42%)

Sources & evidence

ORD record
ord-131c1a1437a44933bd67bf2392d48c28
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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