Diethyl Ether → HCID 67145179, compound

HRID 1968617Notes

Reaction equation

HRID 1968617 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][CH: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]=[CH:27]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 160545-HydroxyindoleHCID 62657Potassium Phosphate, TribasicHCID 2737170Benzoic acid, 2,4-difluoro-, ethyl ester

Product 1

HCID 67145179HCID 67145179, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Ethyl 2,4-difluorobenzoate (1.14 g), K3PO4 (1.30 g) and 5-hydroxyindole (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 aqueous NaOH solution, and brine, and dried over Na2SO4. The solution was then filtered, 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 aqueous NaOH solution, and brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was then filtered
  5. concentrationconcentrated
  6. customthe crude product was chromatographed on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b2713ba36e1b4d4d82634841c2d3a922
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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