Phthalimide → trans-2-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}-1H-isoindole-1,3(2H)-dione

HRID 1639784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639784
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C@@H:12]1[CH2:14][C@H:13]1[CH2:15]O.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:48]1(=[O:58])[NH:52][C:51](=[O:53])[C:50]2=[CH:54][CH:55]=[CH:56][CH:57]=[C:49]12>O1CCCC1.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C@@H:12]1[CH2:14][C@H:13]1[CH2:15][N:52]1[C:48](=[O:58])[C:49]2[C:50](=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:51]1=[O:53]

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66720702trans-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanol

Produkt 1

HCID 66720673trans-2-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}-1H-isoindole-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of trans-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanol (500 mg, 2.27 mmol) in tetrahydrofuran (22 mL) were added a solution (40%, 1.24 mL, 2.72 mmol) of diethyl azodicarboxylate in toluene, triphenylphosphine (774 mg, 2.95 mmol) and phthalimide (434 mg, 2.95 mmol), and the mixture was stirred under nitrogen atmosphere at room temperature for 1.5 hr. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60) to give trans-2-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}-1H-isoindole-1,3(2H)-dione as a crudely purified product (893 mg).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60)

Quellen und Nachweise

ORD-Eintrag
ord-cc8cd5f401554c40880bd8ff20b6448b
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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