Methane → HCID 178493807, 화합물

HRID 59626

반응식

HRID 59626 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19](Br)[C:18]=3[O:24][CH3:25])[C:11]([CH3:26])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C:27]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)([OH:29])=[O:28].[OH-].[K+].C.Cl>C(O)C.O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([O:24][CH3:25])=[C:19]([C:34]4[CH:33]=[CH:32][CH:31]=[C:30]([C:27]([OH:29])=[O:28])[CH:35]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:26])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

참가 물질

10

반응물 5

HCID 297Methane2회HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27339573-Carboxyphenylboronic acidHCID 1784863784-[(3-bromo-2-methoxyphenyl)hydrazinylidene]-2-(3,4-dimethylphenyl)-5-methylpyrazol-3-one

생성물 1

HCID 178493807HCID 178493807, 화합물

시약·촉매·용매 4

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1-(3,4-dimethylphenyl)-3-methyl-4-(3-bromo-2-methoxyphenyl)hydrazono-5-pyrazolone (10 g) prepared as in Example 16, 3-carboxyphenylboronic acid (5.2 g), bis(triphenylphosphine)palladium(II)chloride [PdCl2(PPh3)2] (0.84 g), potassium hydroxide (6.72 g) in ethanol (200 mL) and water (15 mL) was heated to about reflux temperature under nitrogen atmosphere and stirred for about 8 hours. The reaction mixture was cooled to about 30° C. to about 35° C. and stirred for about 4 hours at about the same temperature. The reaction mixture was treated with Norit™ charcoal and filtered over celite bed. The filtrate was treated with EDTA and Scavenger Type 2S. The mixture was stirred at about 30° C. to about 40° C. for about 20 hours and filtered over celite bed. To the filtrate, hydrochloric acid was added to adjust the pH to about 3 to about 5. The mixture was stirred for about 2 hours at about 80° C. to about 85° C. The mixture was cooled to about 40° C. to about 45° C. and filtered. The wet cake was treated with potassium hydroxide in methanol and stirred to give a clear solution. The solution was treated with 50% tributylphosphene in ethyl acetate and stirred for about 20 hours at about room temperature. The pH of the solution was adjusted to about 2 to about 4 using hydrochloric acid and the solid obtained was filtered and purified using tetrahydrofuran. Yield: 9.3 g

후처리

  1. temperaturewas heated
  2. temperatureto about reflux temperature under nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled to about 30° C. to about 35° C.
  4. stirringstirred for about 4 hours at about the same temperature
  5. filtrationfiltered over celite bed
  6. additionThe filtrate was treated with EDTA and Scavenger Type 2S
  7. stirringThe mixture was stirred at about 30° C. to about 40° C. for about 20 hours
  8. filtrationfiltered over celite bed
  9. additionTo the filtrate, hydrochloric acid was added
  10. stirringThe mixture was stirred for about 2 hours at about 80° C. to about 85° C
  11. temperatureThe mixture was cooled to about 40° C. to about 45° C.
  12. filtrationfiltered
  13. additionThe wet cake was treated with potassium hydroxide in methanol
  14. stirringstirred
  15. customto give a clear solution
  16. stirringstirred for about 20 hours at about room temperature
  17. customthe solid obtained
  18. filtrationwas filtered
  19. custompurified

출처 및 근거

ORD 기록
ord-65b5635ca16c4361ba1b694ba355eb5c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440927B2

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