Dimethylformamide → 2-Bromo-5-chloro-3-methoxypyridine

HRID 963232Notes

Reaction equation

HRID 963232 reaction equation
[CH3:1]N(C=O)C.[Br:6][C:7]1[C:12]([OH:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=1.[H-].[Na+].CI>O>[Br:6][C:7]1[C:12]([O:13][CH3:1])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 147400532-Bromo-5-chloropyridin-3-ol

Product 1

HCID 190814342-Bromo-5-chloro-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF (60 mL) solution containing 2-bromo-5-chloro-3-hydroxypyridine (19.95 g, 95.7 mmol) at 0° C. was added NaH (2.53 g, 105.3 mmol) portion wise. After the cessation of H2 evolution, CH3I (14.26 g, 100.5 mmol) was added dropwise and the reaction stirred ~16 h. Water (1.9 mL) was added and the solvent removed under reduced pressure. The concentrate was triturated with 5 portions of CH2Cl2. The combined organic phases were washed with sat. NaCl solution, dried with K2CO3, filtered, and concentrated in vacuo. Silica gel chromatography (95:5 Hexane:EtOAc) of the concentrate afforded the title compound.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe concentrate was triturated with 5 portions of CH2Cl2
  3. washThe combined organic phases were washed with sat. NaCl solution
  4. dry with materialdried with K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02d974ba0a9744c0992196be9d522c6f
Source dataset
uspto-grants-1998_06
Patent number
US05763444

Reaction notes

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