Methyl iodide → Methyl 6-bromo-1-methyl-1H-indole-3-carboxylate

HRID 1689810Notes

Reaction equation

HRID 1689810 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[C:15](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[N:7]([CH3:15])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11499811Methyl 6-Bromo-1H-Indole-3-Carboxylate

Product 1

HCID 57443279Methyl 6-bromo-1-methyl-1H-indole-3-carboxylateYield 88.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 25 g (98.39 mmol) of 6-bromo-1H-indole-3-carboxylic acid methyl ester and 27.20 g (196 mmol) of potassium carbonate in 300 mL of acetonitrile is added at room temperature Methyl Iodide (20.95 g, 147.6 mmol). The reaction mixture is stirred at room temperature for 3 days. The solvent is evaporated, 500 ml of water is added, and the organic layer is extracted with (3×300 ml) ethyl acetate. The organics are combined, dried over magnesium sulfate and evaporated. The crude is purified by silica gel chromatography eluting with hex/EtOAc 8:2. The title compound (23.3 g (88%)) is obtained as a brown solid. MS (m/e): 268 (M+1).

Workup

  1. customThe solvent is evaporated
  2. addition500 ml of water is added
  3. extractionthe organic layer is extracted with (3×300 ml) ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude is purified by silica gel chromatography
  7. washeluting with hex/EtOAc 8:2

Sources & evidence

ORD record
ord-7cdbcb3db3494090b929e3ad423f225a
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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