Methyl iodide → 6-Bromo-1,3-dimethyl-1H-indole

HRID 1051490Notes

Reaction equation

HRID 1051490 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:14]I>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[CH:7][N:8]2[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 534029586-Bromo-3-methyl-1H-indole

Product 1

HCID 233835116-Bromo-1,3-dimethyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-3-methyl-1H-indole (200 mg, 0.95 mmol) in DMF (8 mL) was added NaH (114 mg, 2.85 mmol, m %/60%). The mixture was stirred at room temperature for 1 h before the addition of MeI (162 mg, 1.14 mmol). The system was stirred at room temperature for 4 h then the mixture was quenched with water and extracted with EtOAc. The organic layer was concentrated to give crude product which was used in next step without further purification. LCMS (m/z): 224.1 [M+H]+.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. customto give crude product which
  5. customwas used in next step without further purification

Sources & evidence

ORD record
ord-bd6104608632445aabcb26bc882c55c3
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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