Indole → N-(4-methylphenyl)indole

HRID 1883349Notes

Reaction equation

HRID 1883349 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:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu]I.CCCCCC.C(OCC)(=O)C.O1CCOCC1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 798IndoleHCID 78054-BromotolueneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 9794286N-(4-methylphenyl)indoleYield 95%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using the general procedure outlined in Example 63, indole (0.117 g, 1.00 mmol) was coupled with 4-bromotoluene (185 μL, 1.50 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-1,2-cyclohexanediamine (24 μL, 0.20 mmol, 20 mol %) and dioxane (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 50:1) provided 0.197 g (95% yield) of the product as a white solid. This product was pure by 1H NMR when compared to the known spetra.

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-eabd0a33d3204f20b34c46f367121a2b
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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