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

HRID 2273708Notes

Reaction equation

HRID 2273708 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-dbb84e70f28447b1a8d7a8add64858fd
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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