Isopropyl iodide → 3-Isopropyl-1H-indol-6-amine

HRID 2404660Notes

Reaction equation

HRID 2404660 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.[CH:13](I)([CH3:15])[CH3:14]>CC#N>[CH: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)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 6362Isopropyl iodideHCID 785026-Nitro-1H-indole

Product 1

HCID 451170133-Isopropyl-1H-indol-6-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Isopropyl-1H-indol-6-ylamine (B-13) was synthesized following the general scheme above starting from 6-nitroindole and isopropyl iodide. Overall yield (17%). HPLC ret. time 2.06 min, 10-99% CH3CN, 5 min run; ESI-MS 175.2 m/z (MH+).

Workup

  1. customOverall yield (17%)

Sources & evidence

ORD record
ord-35760dc04ba5447b93500fc42fe7d73c
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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