Diisopropylethylamine → Indole

HRID 249159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249159
NC1C=C(C=CC=1)C([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=O.C(N(C(C)C)CC)(C)C.C(C1C=CC(C(C2C=CC(CC(C)C)=CC=2)Cl)=CC=1)C(C)C>CN(C)C=O>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 19010817Bis(4-isobutylphenyl)chloromethaneHCID 190247263-(3-Aminobenzoyl)indole

Produkt 1

HCID 798IndoleAusbeute 210,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(3-aminobenzoyl)indole (1.2 g) in N,N-dimethylformamide (12 ml) were added diisopropylethylamine (1.77 ml) and a solution of bis(4-isobutylphenyl)chloromethane (1.92 g) in N,N-dimethylformamide (5 ml) at 25° C., and the mixture was allowed to stand at the same temperature for 14 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (50 g) eluting with a mixture of ethyl acetate and chloroform (1:20) to give 3-[3-bis(4-isobutylphenyl)methylamino]benzoyl]indole (1.25 g) as pale yellow amorphous powder.

Aufarbeitung

  1. customat 25° C.
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (50 g)
  7. washeluting with a mixture of ethyl acetate and chloroform (1:20)

Quellen und Nachweise

ORD-Eintrag
ord-99801fe2c9884714a43dcda710968b72
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212320

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