Tetrahydrofuran → (Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-iodo-2H-indol-2-one

HRID 380879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380879
[F:1][C:2]1[C:3]([I:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[C:13]([C:16]1[CH:17]=[C:18]([CH:21]=O)[NH:19][CH:20]=1)(=[O:15])[CH3:14].C1COCC1>N1CCCCC1.CC(O)C>[C:13]([C:16]1[CH:17]=[C:18](/[CH:21]=[C:5]2\[C:6](=[O:11])[NH:7][C:8]3[C:4]\2=[C:3]([I:12])[C:2]([F:1])=[CH:10][CH:9]=3)[NH:19][CH:20]=1)(=[O:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 97956015-Fluoro-4-iodoindolin-2-oneHCID 124151104-Acetyl-1H-pyrrole-2-carboxaldehyde

Produkt 1

HCID 18366029(Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-iodo-2H-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8082PiperidineLösungsmittel

Versuchsvorschrift

1,3-Dihydro-5-fluoro-4-iodo-2H-indol-2-one (0.77 g, 2.8 mmol) (see Example 2A, supra) and 4-acetyl-2-formylpyrrole (0.42 g, 3.06 mmol) (Example 90A above) were suspended in 1% piperidine in 2-propanol (12 mL) and THF (5 mL) and heated at 85° C. for 2 h. Yellow precipitate was formed. After cooling to room temperature, product was collected by filtration and washed with aqueous 2-propanol and dried in vacuum oven to yield (Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-iodo-2H-indol-2-one. (Yield 0.89 g, 80.8%).

Aufarbeitung

  1. customYellow precipitate was formed
  2. filtrationproduct was collected by filtration
  3. washwashed with aqueous 2-propanol
  4. customdried in vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-824ce61f46a54f46afe7696013c4ad7f
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303793B1

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