Diethyl Ether → HCID 67145244, compound

HRID 573144Notes

Reaction equation

HRID 573144 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 1M 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 1M 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-9567e99e20f84fcca4ac265d97061d1a
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

Loading…