Ethyl Acetate → HCID 85652382, compound

HRID 1492481Notes

Reaction equation

HRID 1492481 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11]([O:14][CH2:15][CH3:16])(=[O:13])[CH3:12]>N1C=CC=CC=1.[Cu-]=O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:4]1[CH:3]=[CH:2][CH:10]=[CH:9][C:12]=1[C:11]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 119785-Methylindole

Product 1

HCID 85652382HCID 85652382, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

5-Methylindole (730.6 mg, 5.57 mmol, 1.0 eq.) was combined with the title C compound of Example 1 (3.189 g, 13.9 mmole, 2.5 eq.) and copper(I)oxide (797 mg, 5.57 mmol, 1.0 eq.) in pyridine (5.6 ml, 1M). The reaction was heated at 120° C. for 3 hours, cooled to room temperature, diluted with ethyl acetate and filtered through celite. The filtrate was washed twice with water, twice with aqueous 1N hydrochloric acid, and once with aqueous saturated sodium hydrogen carbonate. The organic phase was then dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on silica gel (50 g) eluting with hexane:ether (40:1) followed by (20:1) to give 848 mg of the title A compound.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through celite
  3. washThe filtrate was washed twice with water, twice with aqueous 1N hydrochloric acid
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. filtrationfiltered through magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (50 g)
  8. washeluting with hexane:ether (40:1)
  9. customto give 848 mg of the title A compound

Sources & evidence

ORD record
ord-8196f4bb942f45e0a3bb5c09ea1a594a
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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