Benzyl Bromide → 1-benzyl-1H-indol-6-amine

HRID 401241

Reaction equation

HRID 401241 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)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC#N>[CH2:13]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=2)[CH:8]=[CH:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 785026-Nitro-1H-indole

Product 1

HCID 220195621-benzyl-1H-indol-6-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Benzyl-1H-indol-6-ylamine (B-2) was synthesized following the general scheme above starting from 6-nitroindole and benzyl bromide. Overall yield (˜40%). HPLC ret. time 2.19 min, 10-99% CH3CN, 5 min run; ESI-MS 223.3 m/z (MH+).

Workup

  1. customOverall yield (˜40%)

Sources & evidence

ORD record
ord-ce9263e82da745e1939b6317a2d5b066
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Linked notes

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