5-Hydroxyindole → HCID 67127040, compound

HRID 574778Notes

Reaction equation

HRID 574778 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.F[C:12]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOCCOC.CCOCC>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][C:12]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:13]=3[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

6

Reactant 3

HCID 160545-HydroxyindoleHCID 62657Potassium Phosphate, TribasicHCID 2782897Methyl 2,4-Difluorobenzoate

Product 1

HCID 67127040HCID 67127040, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8150DiglymeSolvent

Procedure

A mixture of 5-hydroxyindole (8.5 g), methyl 2,4-difluorobenzoate (7.05 g), and K3PO4 (9.32 g) in diglyme (40 mL) at 115° C. was stirred for 24 hours. The reaction was cooled, diluted with ether (600 mL), and washed twice with water, and brine, and concentrated. The crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed twice with water, and brine
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-734578db00b54ac99c12a5518bdee3f7
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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