Methyl iodide → Methyl 4-chloro-1,2-dimethyl-1H-indole-3-carboxylate

HRID 453854Notes

Reaction equation

HRID 453854 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:12]([O:14][CH3:15])=[O:13])=[C:5]([CH3:11])[NH:6]2.[H-].[Na+].[CH3:18]I>CN(C=O)C.[NH4+].[Cl-]>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:12]([O:14][CH3:15])=[O:13])=[C:5]([CH3:11])[N:6]2[CH3:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59473719methyl 4-chloro-2-methyl-1H-indole-3-carboxylate

Product 1

HCID 59473668Methyl 4-chloro-1,2-dimethyl-1H-indole-3-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

Methyl 4-chloro-2-methyl-1H-indole-3-carboxylate (13.45 mmol, 1.0 equiv.) was dissolved in DMF (7 ml) and added at 0° C. to a suspension of NaH (26.90 mmol, 2.0 equiv.) in DMF (13 ml). The mixture was then stirred for 30 min. Methyl iodide (20.17 mmol, 1.5 equiv.) was added dropwise at 0° C. and stirring was carried out for 2 h at 25° C. The reaction mixture was diluted with NH4Cl solution (20 ml) and extracted with ethyl acetate (3×50 ml). The combined organic phases were washed with water and sat. NaCl solution (in each case 50 ml), dried over Na2SO4 and concentrated to dryness under reduced pressure. Yield: 72%

Workup

  1. stirringstirring
  2. waitwas carried out for 2 h at 25° C
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined organic phases were washed with water and sat. NaCl solution (in each case 50 ml),
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7daa7349e05845bdb1ec6c47cb131807
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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