Water → HCID 21249820, compound

HRID 1531644Notes

Reaction equation

HRID 1531644 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.O.[H-].[Na+].C[O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21](Br)[N:20]=1)=[O:18]>CC(N(C)C)=O.[Cu](I)I>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]([OH:18])=[O:16])=[N:20][C:21]=1[O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 10868568Methyl 6-bromo-5-methoxypicolinate

Product 1

HCID 21249820HCID 21249820, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
120 °C

Procedure

3-(trifluoromethyl) phenol (1.317 g, 0.0081 mol) was dissolved in 10 ml of dried dimethyl acetamide. While cooling the obtained solution with water, sodium hydride (0.39 g (ca. 60% in mineral oil), 0.0081×1.2 mol) was added to the solution. After completion of the foaming, a solution obtained by dissolving 6-bromo-5-methoxy-2-pyridine carboxylic acid methyl ester (2.0 g, 0.0081 mol) in 10 ml of dried dimethyl acetamide, and then copper iodide (1.55 g, 0.081 mol) were successively added to the solution. The obtained mixture was heated and stirred at 120° C. for 10 hours. Thereafter, the obtained reaction solution was cooled, mixed with 50 ml of water and then with 50 ml of ethyl acetate, and filtered through a glass filter provided with High-flow Super Cell. The obtained filtrate was extracted with ethyl acetate to obtain an aimed product. An organic phase was separated from the product, washed with water, and then dried with anhydrous sodium sulfate. The dried product was concentrated, and the obtained residues were purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane).

Workup

  1. additionwas added to the solution
  2. customAfter completion of the foaming, a solution obtained
  3. temperatureThe obtained mixture was heated
  4. customThereafter, the obtained reaction solution
  5. temperaturewas cooled
  6. filtrationwith 50 ml of ethyl acetate, and filtered through a glass
  7. filtrationfilter
  8. customprovided with High-flow Super Cell
  9. extractionThe obtained filtrate was extracted with ethyl acetate

Sources & evidence

ORD record
ord-fa5a7d60c4e6452a8c9bb0bfbf4ed607
Source dataset
uspto-grants-2001_03
Patent number
US06200933B1

Reaction notes

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