6-Bromoindole → benzyl (3-(1-(6-bromo-1H-indol-3-yl)-2-nitropropyl)-2-methylphenyl)carbamate

HRID 2361400Notes

Reaction equation

HRID 2361400 reaction equation
[CH3:1][C:2]1[C:7](/[CH:8]=[C:9](/[N+:11]([O-:13])=[O:12])\[CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Br:25][C:26]1[CH:34]=[C:33]2[C:29]([CH:30]=[CH:31][NH:32]2)=[CH:28][CH:27]=1>>[Br:25][C:26]1[CH:34]=[C:33]2[C:29]([C:30]([CH:8]([C:7]3[C:2]([CH3:1])=[C:3]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:4]=[CH:5][CH:6]=3)[CH:9]([N+:11]([O-:13])=[O:12])[CH3:10])=[CH:31][NH:32]2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 6764936-BromoindoleHCID 70651684(E)-benzyl 2-methyl-3-(2-nitroprop-1-enyl)phenylcarbamate

Product 1

HCID 70651981benzyl (3-(1-(6-bromo-1H-indol-3-yl)-2-nitropropyl)-2-methylphenyl)carbamateYield 31.3%

Conditions

Temperature
140 °C

Procedure

A mixture of (E)-benzyl (2-methyl-3-(2-nitroprop-1-en-1-yl)phenyl)carbamate (5.16 g, 15.8 mmol) and 6-bromo-1H-indole (6.20 g, 31.6 mmol) was heated neat at 140° C. overnight. The crude reaction mixture was purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane (20%-35%-50%) to give benzyl (3-(1-(6-bromo-1H-indol-3-yl)-2-nitropropyl)-2-methylphenyl)carbamate (2.58 g, 4.94 mmol, 31% yield) as a burgundy oil/solid and as a 1:1 mixture of diastereomers.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash silica gel chromatography
  3. additiona mixture of ethyl acetate in hexane (20%-35%-50%)

Sources & evidence

ORD record
ord-595d3dd65b9b4400ad6db94d903f6530
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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