Potassium Carbonate → HCID 178466111, compound

HRID 1386893Notes

Reaction equation

HRID 1386893 reaction equation
[CH3:1][C:2]([N:5]1[C:9]([OH:10])=[C:8]([C:11](=[O:24])[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14](I)[C:13]=2[CH3:23])[CH:7]=[N:6]1)([CH3:4])[CH3:3].[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)[CH3:26].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH3:1][C:2]([N:5]1[C:9]([OH:10])=[C:8]([C:11](=[O:24])[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([C:31]3[CH:32]=[CH:33][C:28]([O:27][CH2:25][CH3:26])=[CH:29][CH:30]=3)[C:13]=2[CH3:23])[CH:7]=[N:6]1)([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27343514-Ethoxyphenylboronic acidHCID 178428877HCID 178428877, compound

Product 1

HCID 178466111HCID 178466111, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.0 g (2.2 mmol) of 1-(1,1-dimethylethyl)-5-hydroxy-4-(3-iodo-2-methyl-4-methylsulfonylbenzoyl)pyrazole, 0.541 g (3.3 mmol) of 4-ethoxyphenylboronic acid, 0.607 g (4.4 mmol) of potassium carbonate, 0.025 g (0.11 mmol) of palladium(II) acetate, 0.100 g (0.33 mmol) of tri-o-tolylphosphine, 25 mL of acetonitrile, and 3 mL of water was heated at reflux with stirring for 15 min. The resulting mixture was cooled and diluted with water. The mixture obtained was extracted with ether and acidified with concentrated aqueous hydrochloric acid. The yellow precipitate that formed was collected by filtration and recrystallized by dissolving in dichloromethane and then adding hexane to obtain 800 mg (80 percent of theory) of the title compound as a-white solid melting at 110° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureThe resulting mixture was cooled
  4. customThe mixture obtained
  5. extractionwas extracted with ether
  6. customThe yellow precipitate that formed
  7. filtrationwas collected by filtration
  8. customrecrystallized
  9. dissolutionby dissolving in dichloromethane

Sources & evidence

ORD record
ord-3e1ce6c799b847f8b838b8a397961f9b
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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