Water → HCID 15457042, compound

HRID 1385917Notes

Reaction equation

HRID 1385917 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([C:12]2[C:13](=[O:27])[C:14]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]([C:18]([F:21])([F:20])[F:19])[NH:16][CH:17]=2)=[C:4]([F:28])[CH:3]=1.[H-].[Na+].[CH3:31]I.O>CN(C=O)C>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][C:5]([C:12]2[C:13](=[O:27])[C:14]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]([C:18]([F:21])([F:19])[F:20])[N:16]([CH3:31])[CH:17]=2)=[C:4]([F:28])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15457041HCID 15457041, compound

Product 1

HCID 15457042HCID 15457042, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g (47 mol) of 5-(4-chloro-2-fluoro-5- isopropoxyphenyl)-3-ethoxycarbonyl-2-trifluoromethyl-4(1H)-pyridone was dissolved in 150 ml of DMF, and 2.1 g (53 mmol) of 60% sodium hydride was added thereto under cooling with ice, followed by stirring at room temperature for 15 minutes. Then, 14 g (99 mmol) of methyl iodide was added thereto. After stirring at room temperature for 8 hours, the reaction solution was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and then, the obtained residue was purified by silica gel column chromatography to obtain 6 g (yield: 28%) of the desired product. Melting point: 170-172° C. 1H-NMR (400 MHz, CDCl3) δ value: 1.40(9H,m), 3.85(3H,s), 4.40(2H,q), 4.51(1H,m), 7.17(1H,d), 7.40(1H,d), 7.63(1H,s)ppm.

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring at room temperature for 8 hours
  3. extractionextracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-750a5b30d48b44d8a890d63799e2e8d5
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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