Indole → 1-(2-Aminophenyl)indole

HRID 2179246Notes

Reaction equation

HRID 2179246 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CCCCCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[NH2:13][C:12]1[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=1[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

8

Reactant 4

HCID 798IndoleHCID 119922-BromoanilineHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 115139881-(2-Aminophenyl)indoleYield 71.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using the general procedure, indole (0.117 g, 1.00 mmol) was coupled with 2-bromoaniline (0.206 g, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %) and toluene (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 5:1) provided 0.148 g (71% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.64 (m, 1H), 7.18 (m, 6H), 6.82 (m, 2H), 6.64 (m, 1H), 3.52 (bs, 2H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-8ef113ea5bf24d0683edf0a4bed7db42
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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