Diethyl Ether → HCID 67145244, compound

HRID 1848901Notes

Reaction equation

HRID 1848901 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]=[CH:25][NH:26]2.CCOCC>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:25]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62657Potassium Phosphate, TribasicHCID 754211H-indol-4-olHCID 2782897Methyl 2,4-Difluorobenzoate

Product 1

HCID 67145244HCID 67145244, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Methyl 2,4-difluorobenzoate (1.53 g), K3PO4 (1.89 g) and 4-hydroxyindole (1.08 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 1 M aqueous NaOH solution, and brine, and dried over Na2SO4. 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 1 M aqueous NaOH solution, and brine
  3. dry with materialdried over Na2SO4
  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-63cf9819bff745579f10d5eaee253837
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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