Dimethylformamide → HCID 86683858, compound

HRID 2406710Notes

Reaction equation

HRID 2406710 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH:6]=O)[CH3:5].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2C=CN[CH:16]=2)[CH:14]=1.CI>O>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:6][N:4]([CH3:5])[CH:3]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86683856HCID 86683856, compound

Product 1

HCID 86683858HCID 86683858, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in oil) (6 mg) was added to a DMF (1 ml) solution containing 3-bromo-5-(1H-pyrrol-3-yl)pyridine (28 mg), followed by stirring. Methyl iodide (9 μl) was added, followed by stirring at room temperature for 3 hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=30:1 to 3:1), and a white solid of 3-bromo-5-(1-methyl-1H-pyrrol-3-yl)pyridine (18 mg) was thus obtained.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=30:1 to 3:1)

Sources & evidence

ORD record
ord-7901cb506ae24d479782915496b26519
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

Loading…