Phthalic Anhydride → 2-((5-Bromo-3-chloropyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 587246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587246
Cl.[Br:2][C:3]1[CH:4]=[C:5]([Cl:11])[C:6]([CH2:9][NH2:10])=[N:7][CH:8]=1.[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>C1(C)C=CC=CC=1>[Br:2][C:3]1[CH:4]=[C:5]([Cl:11])[C:6]([CH2:9][N:10]2[C:15](=[O:16])[C:14]3[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12]2=[O:17])=[N:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 6811Phthalic AnhydrideHCID 71138342(5-Bromo-3-chloropyridin-2-yl)methanamine hydrochloride

Produkt 1

HCID 711385752-((5-Bromo-3-chloropyridin-2-yl)methyl)isoindoline-1,3-dioneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of (5-bromo-3-chloropyridin-2-yl)methanamine hydrochloride (0.3 g, 1.4 mmol) in toluene (40 mL) was added TEA (0.41 g, 4.08 mmol) and phthalic anhydride (0.24 g, 1.63 mmol), and the reaction mixture was heated at reflux for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and extracted with EtOAc. The combined EtOAc layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (20-30% EtOAc in hexane) to afford the title compound as a white solid (0.25 g, 65%): 1H NMR (400 MHz, CDCl3) δ 8.78 (s, 1H), 8.45 (s, 1H), 7.88 (m, 2H), 7.74 (m, 2H), 4.56 (m, 2H); ESIMS m/z 349 ([M−H]−); IR (thin film) 3307, 1665, 1114, 813 cm−1.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (20-30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9e690d5cf91343f0811e1d5679081ce9
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226500B2

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