Diethyl Ether → HCID 67145244, compound

HRID 1968616Notes

Reaction equation

HRID 1968616 reaction equation
F[C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=N[NH:26]2.[CH3:31]COCC>COCCOCCOC>[NH:26]1[C:27]2[C:23](=[C:22]([O:21][C:2]3[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=3[C:4]([O:6][CH3:7])=[O:5])[CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:31]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62657Potassium Phosphate, TribasicHCID 2782897Methyl 2,4-DifluorobenzoateHCID 1357424501H-indazol-4-ol

Product 1

HCID 67145244HCID 67145244, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Methyl 2,4-difluorobenzoate (2 g, 11.6 mmol)), K3PO4 (2.4 g, 11.3 mmol) and 4-hydroxyindazole (1.40 g, 10.5 mmol) were stirred at 115° C. in diglyme (20 mL) for 24 hours. The reaction was cooled and poured into ether. The solution was washed three times with 1M NaOH solution, followed by brine, and then dried over Na2SO4 and filtered. The filtrate was then concentrated, and the crude product was chromatographed on silica gel with 20% ethyl acetate/hexanes.

Workup

  1. temperatureThe reaction was cooled
  2. washThe solution was washed three times with 1M NaOH solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was then concentrated
  6. customthe crude product was chromatographed on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-36f9f8984e854c04846b3a6d494d335d
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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