Methyl iodide → N-(1-methoxy-2,2,2-trifluoroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250501Notes

Reaction equation

HRID 1250501 reaction equation
[OH:1][CH:2]([NH:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:11]=1)=[O:9])[C:3]([F:6])([F:5])[F:4].[H-].[Na+].[CH3:31]I>ClCCl.CN(C=O)C.CCCCCC>[CH3:31][O:1][CH:2]([NH:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=2)[N:11]=1)=[O:9])[C:3]([F:6])([F:5])[F:4]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18326210N-(1-hydroxy-2,2,2-trifluoroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Product 1

HCID 18326218N-(1-methoxy-2,2,2-trifluoroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

0.6 g (0.0015 mol) of N-(1-hydroxy-2,2,2-trifluoroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide was dissolved in a mixed solvent of dichloromethane and DMF. The obtained solution was mixed with 0.064 g (ca. 60% in mineral oil; 0.0015×1.1 mol) of NaH and then with 0.42 g (0.0015×2.0 mol) of methyl iodide, followed by treating the solution under reflux for about 8 hours. The reaction solution was distributed in hexane-saturated sodium bicarbonate water and washed with saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. additionby treating the solution
  2. temperatureunder reflux for about 8 hours
  3. washwashed with saturated brine
  4. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1f511ce22b314176854b4d9d9b8a07f5
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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