Dimethylformamide → 3-Bromo-5-(methoxymethyl)pyridine

HRID 2406727Notes

Reaction equation

HRID 2406727 reaction equation
[H-].[Na+].[CH3:3]N(C=O)C.[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][OH:16])[CH:12]=[N:13][CH:14]=1.CI>O>[Br:8][C:9]1[CH:14]=[N:13][CH:12]=[C:11]([CH2:15][O:16][CH3:3])[CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 186245693-Bromo-5-(methoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (61% in oil) (11 mg) was added to a DMF (0.9 ml) solution containing (5-bromopyridin-3-yl)methanol (34 mg) under ice cooling, followed by stirring for 1 hour. Then, methyl iodide (17 μl) was added, followed by stirring at room temperature for 13 hours. Thereafter, water was added to the reaction solution, 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=4:1 to 1:1), and a light yellow solid of 3-bromo-5-(methoxymethyl)pyridine (26.5 mg) was thus obtained.

Workup

  1. stirringby stirring at room temperature for 13 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. distillationSubsequently, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-e1082d0e363c43d0aa8d61add23daec5
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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