Methyl iodide → 1-Methyl-6-nitro-2-phenyl-1H-indole

HRID 1896789Notes

Reaction equation

HRID 1896789 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:19]1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].CI>O1CCCC1>[CH3:19][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[C:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2855718-Crown-6HCID 207598016-Nitro-2-phenyl-1H-indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 214325091-Methyl-6-nitro-2-phenyl-1H-indoleYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-nitro-2-phenyl-1H-indole (106 mg, 0.44 mmol) and 18-Crown-6 (130 mg, 0.49 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature was added potassium tert-butoxide (55 mg, 0.49 mmol) followed by methyl iodide (31 μL, 0.49 mmol). The solution was stirred at room temperature for 30 min. Tetrahydrofuran was removed in vacuo. Ethyl acetate was added, and the organic layer was washed with water and then brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 110 mg (98%) of the title compound.

Workup

  1. customTetrahydrofuran was removed in vacuo
  2. additionEthyl acetate was added
  3. washthe organic layer was washed with water
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-dfb4c4ff2bbf4ab9a1f5930c4bfab12f
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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