Methyl iodide → 2-(5-bromo-7-fluoro-4-methoxy-1-methyl-1H-indol-3-yl)-N,N-dimethylacetamide

HRID 1404091Notes

Reaction equation

HRID 1404091 reaction equation
[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14].[OH-].[K+].[CH3:22]I>CN(C=O)C>[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:22])[CH:6]=[C:5]2[CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 669271532-(5-bromo-7-fluoro-4-methoxy-1H-indol-3-yl)-N,N-dimethylacetamide

Product 1

HCID 669270242-(5-bromo-7-fluoro-4-methoxy-1-methyl-1H-indol-3-yl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 8-10 (7.0 g, 21.3 mmol) in anhydrous DMF (20 mL) was added KOH (4.34 g, 78.0 mmol), and MeI (4.55 g, 32.0 mmol) at room temperature. After the mixture was stirred for 1 h, TLC showed that the reaction was completed. The mixture was quenched with water and extracted with ethyl acetate (150 mL×3). The organic layers were combined and concentrated in vacuo. 8-11 (7.2 g, crude) was obtained as yellow oil and used for the next step without further purification.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate (150 mL×3)
  3. concentrationconcentrated in vacuo
  4. custom8-11 (7.2 g, crude) was obtained as yellow oil
  5. customused for the next step without further purification

Sources & evidence

ORD record
ord-757e061c3161449d868cc28fdac45355
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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