Triethylamine → HCID 178481843, compound

HRID 1241237Notes

Reaction equation

HRID 1241237 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[C:8](=O)([O-])[O-:9].[K+].[K+].C(N(CC)CC)C.Br[C:22]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[C:30]2[C:23]=1[CH2:24][CH:25]1[CH2:29][O:28][N:27]=[C:26]12.[C]=O>O1CCOCC1>[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([C:22]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[C:30]2[C:23]=1[CH2:24][CH:25]1[CH2:29][O:28][N:27]=[C:26]12)=[O:9]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 11370490HCID 11370490, compoundHCID 178418416HCID 178418416, compound2×HCID 178481816HCID 178481816, compound

Product 1

HCID 178481843HCID 178481843, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
1300 °C

Procedure

0.62 g (6.33 mmol) of 5-hydroxy-1-methylpyrazole, 1.75 g (12.66 mmol) of dry potassium carbonate, 1.28 g (12.67 mmol) of triethylamine and 0.22 g (0.30 mmol) of bis-(triphenylphosphane)palladium dichloride were added to a suspension of 2.0 g (6.33 mmol) of 5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole in 100 ml of dioxane. In a miniautoclave, a carbon monoxide pressure of 20 bar was applied, the mixture was stirred for 5 minutes and the autoclave was vented. This procedure was repeated 3 times. The autoclave was subsequently heated to 1300° C., a carbon monoxide pressure of 20 bar was applied once more and the mixture was stirred for 24 hours. After cooling and venting, the solvent was removed, and the residue was taken up in water, adjusted to pH 11 and washed with methylene chloride. The mixture was subsequently acidified to pH 4 using 10 percent strength hydrochloric acid and extracted with methylene chloride. The combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 0.58 g (25%) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazole)-methanone in the form of a dark oil.

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. washwashed with methylene chloride
  5. extractionextracted with methylene chloride
  6. washThe combined organic phases were washed with saturated ammonium chloride solution
  7. customdried
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-7300d1dd3039468b9014f5326c60948e
Source dataset
uspto-grants-2006_10
Patent number
US07115545B1

Reaction notes

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