Diethyl Ether → ethyl 2-(1H-indazol-5-yloxy)-4-fluorobenzoate

HRID 1518794Notes

Reaction equation

HRID 1518794 reaction equation
F[C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[CH:26]2.CCOCC>COCCOCCOC>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([O:22][C:2]3[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=3[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:31][CH:30]=2)[CH:26]=[N:27]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62657Potassium Phosphate, TribasicHCID 1014381H-Indazol-5-olHCID 2737170Benzoic acid, 2,4-difluoro-, ethyl ester

Product 1

HCID 67225497ethyl 2-(1H-indazol-5-yloxy)-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Ethyl 2,4-difluorobenzoate (1.14 g), K3PO4 (1.30 g) and 5-hydroxyindazole (0.90 g) were stirred at 110° C. in diglyme (12 mL) for 24 hours. The reaction was cooled and poured into ether. The solution was washed three times with 1M NaOH solution, and brine, and dried. The solution 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, and brine
  3. customdried
  4. concentrationThe solution was then concentrated
  5. customthe crude product was chromatographed on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5ab679896fa3463a8f3f89c18713cf7b
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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