Methyl iodide → HCID 86683864, compound

HRID 340479Notes

Reaction equation

HRID 340479 reaction equation
C(=O)([O-])[O-].[K+].[K+].CI.[CH3:9][N:10]([CH3:14])[C:11](=O)[CH3:12].[Br:15][C:16]1[CH:17]=[C:18]([C:22]2C=C([CH:26]=[CH:27][CH:28]=2)N)[CH:19]=[N:20][CH:21]=1>O>[Br:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:12]=[C:11]([CH:26]=[CH:27][CH:28]=2)[N:10]([CH3:14])[CH3:9])[CH:19]=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 23298104HCID 23298104, compound

Product 1

HCID 86683864HCID 86683864, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (83 mg) and methyl iodide (62 W) were added to an N,N-dimethylacetamide (1 ml) solution containing 3-(5-bromopyridin-3-yl)aniline (50 mg), followed by stirring at 80° C. for 4 hours. Water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 3:1), and a white solid of 3-(5-bromopyridin-3-yl)-N,N-dimethylaniline (7.1 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 3:1)

Sources & evidence

ORD record
ord-b0386c0f562a4d4288e3241af558cf88
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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