2-Methylindole → 1-(4-Methoxyphenyl)-2-methyl-1H-indole

HRID 491016Notes

Reaction equation

HRID 491016 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.N[C@@H]1CCCC[C@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 72242-MethylindoleHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 696764-Iodoanisole

Product 1

HCID 120796281-(4-Methoxyphenyl)-2-methyl-1H-indoleYield 74%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

1-(4-Methoxyphenyl)-2-methyl-1H-indole was synthesized according to Buchwald et al. J. Am. Chem. Soc. 2001, 123, 7727. 2-Methylindole (157 mg, 1.2 mmol), 4-iodoanisole (234 mg, 1 mmol), copper(I) iodide (2 mg, 0.01 mmol), trans-1,2-diaminocyclohexane (11.4 mg, 0.1 mmol), and potassium phosphate tribasic (446 mg, 2.1 mmol) were stirred in dioxane (1 mL) at 90° C. overnight. The reaction mixture was filtered through a pad of silica and washed with ethyl acetate. SiO2 chromatography with 5-20% ethyl acetate/hexanes gave 175 mg of the desired product (74% yield). LC-MS (C16H15NO calc'd 237) m/z 238 (M+H).

Workup

  1. custom1-(4-Methoxyphenyl)-2-methyl-1H-indole was synthesized
  2. filtrationThe reaction mixture was filtered through a pad of silica
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7b930d524ff447dcae0d34c1c23869da
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Reaction notes

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