p-Toluenesulfonic acid monohydrate → (S)-methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetate

HRID 132454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132454
Br[C:2]1[C:10]2[C:5](=[C:6]([Br:24])[CH:7]=[C:8]([CH2:13][C@@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17][CH3:18])=[O:16])[C:9]=2CO)[NH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:24][C:6]1[C:5]2[NH:4][N:3]=[CH:2][C:10]=2[C:9]2[CH2:18][O:17][C:15](=[O:16])[C@H:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:13][C:8]=2[CH:7]=1

Komponenten

5

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178500724(S)-dimethyl 2-((3,7-dibromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate

Produkt 1

HCID 59732087(S)-methyl 2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-Dimethyl 2-((3,7-dibromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinate (440 mg, 1.065 mmol) was dissolved in toluene (30 mL). p-Toluenesulfonic acid monohydrate (28 mg, 0.147 mmol) was added to the mixture. Reaction was warmed to reflux and held for 18 hours with stirring. Mixture was cooled to room temperature and then diluted with ethyl acetate. Material was washed with aqueous sodium bicarbonate and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as amber oil in 42% yield. MS (M+H)+=367.2, 369.2.

Aufarbeitung

  1. customReaction
  2. temperaturewas warmed
  3. temperatureto reflux
  4. washMaterial was washed with aqueous sodium bicarbonate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. washSilica gel chromatography eluting ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-324c5f78140841f7917e552776197a67
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

Notizen zur Reaktion

Wird geladen…