Pyridine → 1-(6-Bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-1-yl)ethanone

HRID 1618499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618499
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[C:6]2[N:8]([C:22](=[O:24])[CH3:23])[CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 582218836-Bromo-1,2-dihydrospiro(indole-3,4'-oxane)

Produkt 1

HCID 672853631-(6-Bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-1-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (2.53 g, 9.44 mmol) was dissolved in pyridine (8.39 mL, 104 mmol) and acetic anhydride (1.34 mL, 14.2 mmol) was added followed by DMAP (0.0576 g, 0.472 mmol). The reaction was heated to 85° C. for 90 min. After this time the reaction was concentrated in vacuo and the resulting oil was partitioned between EtOAc and 0.5N HCl. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to give 1-(6-bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-yl)ethanone.

Aufarbeitung

  1. concentrationAfter this time the reaction was concentrated in vacuo
  2. customthe resulting oil was partitioned between EtOAc and 0.5N HCl
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3f7aee9c982f4324b68eb03befddf701
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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