Triethylamine → {3-[(E)-2-(4-Fluorophenyl)vinyl]-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl}carbamic Acid Tert-Butyl Ester

HRID 34110

Reaktionsgleichung

Reaktionsgleichung von HRID 34110
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:9]=[C:10]2[C:16](I)=[N:15][N:14]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]2=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].[F:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[CH2:44])=[CH:41][CH:40]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:9]=[C:10]2[C:16](/[CH:44]=[CH:43]/[C:42]3[CH:45]=[CH:46][C:39]([F:38])=[CH:40][CH:41]=3)=[N:15][N:14]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]2=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68926908(3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic Acid Tert-Butyl Ester

Produkt 1

HCID 68931002{3-[(E)-2-(4-Fluorophenyl)vinyl]-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl}carbamic Acid Tert-Butyl EsterAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 400 mg of (3-iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic acid tert-butyl ester and 162 mg of 4-fluorostyrene in 2.0 mL of N,N-dimethylformamide were added 15 mg of palladium acetate, 40 mg of 2-(di-tert-butylphosphino)biphenyl and 0.46 mL of triethylamine at room temperature, and stirred at 80° C. for 6 hours. After diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-dichloromethane:n-hexane=1:1-ethyl acetate:n-hexane=1:3). The resultant crystals were washed with diethyl ether, to afford 270 mg of the title compound as colorless crystals.

Aufarbeitung

  1. washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-dichloromethane:n-hexane=1:1-ethyl acetate:n-hexane=1:3)
  6. washThe resultant crystals were washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5bc733d0f6204d94be8247f1050b8975
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

Verknüpfte Notizen

Wird geladen…