Triethylamine → HCID 178428868, compound

HRID 49669Notes

Reaction equation

HRID 49669 reaction equation
Br[C:2]1[C:3]([CH3:17])=[C:4]([C:12]2[CH2:16][CH2:15][O:14][N:13]=2)[C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:18][N:19]1[C:23]([OH:24])=[CH:22][CH:21]=[N:20]1.[C:25](=O)([O-])[O-:26].[K+].[K+].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH3:18][N:19]1[C:23]([OH:24])=[C:22]([C:25](=[O:26])[C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([C:12]3[CH2:16][CH2:15][O:14][N:13]=3)[C:3]=2[CH3:17])[CH:21]=[N:20]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 109470753-(3-Bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazoleHCID 178481816HCID 178481816, compound

Product 1

HCID 178428868HCID 178428868, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

2.2 l of 1,4-dioxane, 100 g (0.315 mol) of 3-(3-bromo-2-methyl-6-methylsulfonylphenyl)-4,5-dihydroisoxazole, 30.82 g (0.315 mol) of 1-methyl-5-hydroxypyrazole, 87 g (0.63 mol) of potassium carbonate, 63.5 g (0.63 mol) of triethylamine and 11.2 g (0.016 mol) of bis(triphenylphosphine)-palladium dichloride were added to a 3.5 l autoclave. The autoclave was then flushed twice with nitrogen, a carbon monoxide pressure of 10 kg/cm2 was applied and the mixture was heated with stirring to 130° C. The carbon monoxide pressure was increased to 20 kg/cm2 and the mixture was stirred at 130° C. for 24 h. The mixture was then concentrated under reduced pressure and the residue was taken up in water. The aqueous phase of pH 11 was extracted with dichloromethane. The organic phase is discarded. The aqueous phase is adjusted to pH 4 using 18% strength hydrochloric acid. The precipitate was filtered off, washed three times with water and dried at 40° C. under reduced pressure. This gives 85 g of product. The filtrate is extracted with dichloromethane. The organic phase is dried with sodium sulfate, and the solvent is then removed under reduced pressure, giving a further 12.7 g of product.

Workup

  1. customThe autoclave was then flushed twice with nitrogen
  2. temperaturethe mixture was heated
  3. temperatureThe carbon monoxide pressure was increased to 20 kg/cm2
  4. stirringthe mixture was stirred at 130° C. for 24 h
  5. concentrationThe mixture was then concentrated under reduced pressure
  6. extractionThe aqueous phase of pH 11 was extracted with dichloromethane
  7. filtrationThe precipitate was filtered off
  8. washwashed three times with water
  9. customdried at 40° C. under reduced pressure
  10. extractionThe filtrate is extracted with dichloromethane
  11. dry with materialThe organic phase is dried with sodium sulfate
  12. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-b10cfe3058f944dc843a68922384baae
Source dataset
uspto-grants-2004_03
Patent number
US06706886B2

Reaction notes

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