Potassium Carbonate → HCID 19086731, compound

HRID 1464569Notes

Reaction equation

HRID 1464569 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:22]=[C:23]([F:26])[C:24]=1F.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C.CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([C:27]([F:28])([F:29])[F:30])[CH:22]=[C:23]([F:26])[C:24]=1[O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 2736496Benzene, 1-chloro-2,3-difluoro-5-(trifluoromethyl)-HCID 135800032HCID 135800032, compound

Product 1

HCID 19086731HCID 19086731, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Ethyl 2-(6-hydroxyindazol-1-yl)propionate (30 mgs) was dissolved in 0.72 cm3 of a mixture of dry methyl isobutyl ketone (6cm3) and 1 drop of dry DMF. 3-chloro-4,5-difluorobenzotrifluoride (42 mg) and dry potassium carbonate (27mg) were added. The mixture was stirred and heated under reflux for 7 hours, additional dry potassium carbonate being added after 3 hours. After cooling, the solvents were removed under vacuum and diethyl ether added to the residue, the mixture filtered and the inorganic portion washed thoroughly with diethyl ether. The combined ethereal filtrate was concentrated under vacuum and the residue purified by chromatography (SiO2 ; hexane:t-butylmethylether,4:1) to give compound 1, ethyl 2-[6-(2-chloro- 4-trifluoromethyl-6-fluorophenoxy) indazol-1-yl]propionate (29 mg). M+ =430.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 7 hours
  3. temperatureAfter cooling
  4. customthe solvents were removed under vacuum and diethyl ether
  5. additionadded to the residue
  6. filtrationthe mixture filtered
  7. washthe inorganic portion washed thoroughly with diethyl ether
  8. concentrationThe combined ethereal filtrate was concentrated under vacuum
  9. customthe residue purified by chromatography (SiO2 ; hexane:t-butylmethylether,4:1)

Sources & evidence

ORD record
ord-cc12354116b145068d706469ec530aa3
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

Loading…