Methyl iodide → 1-METHOXY-6-CHLORO-2-(TRIFLUOROMETHYL)-1H-IMIDAZO(4,5-b)PYRIDINE

HRID 1580082Notes

Reaction equation

HRID 1580082 reaction equation
[OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13].CI.[C:18](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:18][O:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 30824181-Hydroxyfluromidine

Product 1

HCID 203599161-METHOXY-6-CHLORO-2-(TRIFLUOROMETHYL)-1H-IMIDAZO(4,5-b)PYRIDINE

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Hydroxy-6-chloro-2-(trifluoromethyl)-1H-imidazo-(4,5-b)pyridine (5 grams), 80 milliliters of acetone, 5 milliliters of methyl iodide, and 10 grams of anhydrous potassium carbonate were mixed, heated and refluxed with stirring for 12 hours. The reaction mixture was then filtered, evaporated and eluted off of a silica column with diethyl ether, yielding the desired 1-methoxy-6-chloro-2-(trifluormethyl)-1H-imidazo(4,5-b)pyridine product. It was recrystallized from petroleum ether (boiling at 60°-80°C.). The product so obtained melted at 91°-2°C.

Workup

  1. temperatureheated
  2. temperaturerefluxed
  3. filtrationThe reaction mixture was then filtered
  4. customevaporated
  5. washeluted off of a silica column with diethyl ether

Sources & evidence

ORD record
ord-8dd8a06910964a3fa74245fd638ba622
Source dataset
uspto-grants-1976_01
Patent number
US03932428

Reaction notes

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