Methyl iodide → Methyl 4-bromo-1-methyl-1H-indole-2-carboxylate

HRID 1384816Notes

Reaction equation

HRID 1384816 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2.[H-].[Na+].I[CH3:18]>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:6]2[CH3:18]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4714973methyl 4-bromo-1H-indole-2-carboxylate

Product 1

HCID 21183752Methyl 4-bromo-1-methyl-1H-indole-2-carboxylate

Procedure

The preparation is carried out as in Example 1.1, from 20 g (79 mmol) of methyl 4-bromo-1H-indole-2-carboxylate, from 3.8 g of 60% sodium hydride and from 6 ml of iodomethane. After reaction, the solvent is evaporated under reduced pressure and the residue is taken up in water. The mixture is extracted with ethyl acetate. The organic phase is dried and the solvent is evaporated under reduced pressure. The product is dried under reduced pressure. 20.6 g (77 mmol) of solid are obtained.

Workup

  1. customAfter reaction
  2. customthe solvent is evaporated under reduced pressure
  3. extractionThe mixture is extracted with ethyl acetate
  4. customThe organic phase is dried
  5. customthe solvent is evaporated under reduced pressure
  6. customThe product is dried under reduced pressure

Sources & evidence

ORD record
ord-d671a969ca144b76858bc53ad870d191
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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