Methyl iodide → Ethyl 5-bromo-1-methyl-1H-indole-2-carboxylate

HRID 1689784Notes

Reaction equation

HRID 1689784 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[C:16](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:16])[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 259091Ethyl 5-Bromoindole-2-carboxylate

Product 1

HCID 11637730Ethyl 5-bromo-1-methyl-1H-indole-2-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In dimethylformamide (5 mL), combine ethyl 5-bromo-1H-indole-2-carboxylate (1.00 g, 13.7 mmole), potassium carbonate (1.4 g, 10 mmole), and methyl iodide (280 μL, 4.50 mmole). Heat the mixture to 50° C. for 18 hours. Cool to room temperature and partition between EtOAc and water. Extract with EtOAc (3×), wash with brine (3×), dry (MgSO4) and concentrate to provide crude material. The crude material is purified on 120 g silica gel with 0 to 50% EtOAc in heptane to give 850 mg (81%) of the title compound. ES/MS m/e (81Br) 284.0 (M+H)+.

Workup

  1. temperatureCool to room temperature
  2. custompartition between EtOAc and water
  3. extractionExtract with EtOAc (3×)
  4. washwash with brine (3×)
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate
  7. customto provide crude material
  8. customThe crude material is purified on 120 g silica gel with 0 to 50% EtOAc in heptane

Sources & evidence

ORD record
ord-3954a8ae7b56454db904563d55a67d8d
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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