Indole → 1-Phenyl-1H-indole

HRID 1751932Notes

Reaction equation

HRID 1751932 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.I[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 798IndoleHCID 11575Iodobenzene

Product 1

HCID 1820291-Phenyl-1H-indole

Procedure

Following General Procedure A (90° C., 30 hours), 1H-indole (176 mg, 1.5 mmol) is coupled with iodo-benzene (112 μL, 1.0 mmol). The crude brown oil is purified by flash chromatography on silica gel (eluent: hexanes) to provide 180 mg (93% isolated yield) of the desired product as a light green oil.

Workup

  1. customThe crude brown oil is purified by flash chromatography on silica gel (eluent: hexanes)
  2. customto provide

Sources & evidence

ORD record
ord-4afd82be9e7648e5a8dd98efbb7a1871
Source dataset
uspto-grants-2015_10
Patent number
US09162953B2

Reaction notes

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