Phthalimide → 2-((2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dione

HRID 623462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623462
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][CH:6]=[C:5]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:4]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])=[CH:7][CH:6]=[C:5]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:4]=1

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 67509554(2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanol

Produkt 1

HCID 675086782-((2-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methyl)isoindoline-1,3-dioneAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of (2-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)methanol (1.19 g, 5.02 mmol, Step-2), phthalimide (0.74 g, 5.02 mmol), di-tert-butyl azodicarboxylate (1.05 g, 6.02 mmol) and triphenylphosphine (1.97 g, 7.53 mmol) in tetrahydrofuran (50 mL) is stirred at room temperature for 20 hours. The reaction mixture is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (6:1) to give 0.67 g (37% yield) of the title compound as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (6:1)

Quellen und Nachweise

ORD-Eintrag
ord-1d1aef006f154b83b0e21169cc08d048
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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