Diethyl Ether → ethyl 4-fluoro-2-(2-methyl-1H-indol-5-yloxy)benzoate

HRID 1848808Notes

Reaction equation

HRID 1848808 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+].[CH3:22][C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([OH:32])=[CH:27][CH:26]=2.CCOCC>COCCOCCOC>[F:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([O:32][C:28]2[CH:29]=[C:30]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23]([CH3:22])=[CH:31]3)[CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62657Potassium Phosphate, TribasicHCID 833362-methyl-1H-indol-5-olHCID 2737170Benzoic acid, 2,4-difluoro-, ethyl ester

Product 1

HCID 67227223ethyl 4-fluoro-2-(2-methyl-1H-indol-5-yloxy)benzoate

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Ethyl 2,4-difluorobenzoate (1.14 g), K3PO4 (1.30 g) and 2-methyl-5-indolol (0.90 g) were stirred at 110° C. in diglyme (12 mL) for 24 hours. The mixture was cooled and poured into ether. The solution was washed three times with 1M NaOH solution, and with brine, and dried. The solution was then concentrated. The concentrate was chromatographed on silica gel with 10% ethyl acetate/hexanes.

Workup

  1. temperatureThe mixture was cooled
  2. washThe solution was washed three times with 1M NaOH solution
  3. dry with materialwith brine, and dried
  4. concentrationThe solution was then concentrated
  5. customThe concentrate was chromatographed on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fea484eebfca4ba493caef0877532eb1
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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