HCID 18669064, compound → HCID 53870927, compound

HRID 1058943Notes

Reaction equation

HRID 1058943 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:5]2[C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19].[PH2]([O-])=O.[Na+]>[Pd].O1CCOCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:5]2[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 2

HCID 18669064HCID 18669064, compoundHCID 178527019HCID 178527019, compound3×

Product 1

HCID 53870927HCID 53870927, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst3×HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of palladium on carbon (10%, 1 g) in dioxane (50 mL) was added to a solution of ethyl 5-methyl-α-oxo-2-phenyl-1H-indole-3-acetate (Description 4, 3.66 g) in dioxane (250 mL). A solution of sodium hypophosphite (10 g) in water (10 mL) was added and the mixture was heated under reflux for 10 h. Further palladium on carbon (10%, 1 g) and sodium hypophosphite (10 g) were added and the mixture was heated under reflux for 24 h. Further palladium on carbon (10%, 1 g) and sodium hypophosphite (10 g) were added and the mixture was heated under reflux for 24 h. The mixture was cooled, filtered through celite and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc (90:10) to give the title compound as a colourless solid (1.6 g, 47%). 1H NMR (360 MHz, CDCl3) δ0.86 (3H, t, J 7 Hz), 2.43 (3H, s), 3.73 (2H, s), 4.11-4.16 (2H, m), 6.96 (1H, dd, J 8, 1.8 Hz), 7.18 (1H, d, J 10.8 Hz), 7.28-7.46 (5H, m), 7.58 (1H, d, J 7.2 Hz), and 7.98 (1H, br s). m/z (ES+) 294 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 h
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 24 h
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 24 h
  7. temperatureThe mixture was cooled
  8. filtrationfiltered through celite
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc (90:10)

Sources & evidence

ORD record
ord-95a966c22906465e9490389e724cc085
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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