1,10-Phenanthroline → HCID 69516007, Verbindung

HRID 971158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971158
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:21][C:22]([C:24]1[C:32]2[CH2:31][CH2:30][NH:29][C:28](=[O:33])[C:27]=2[N:26]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[N:25]=1)=[O:23])[CH3:20].C([O-])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CS(C)=O.[Cu]I.CCOC(C)=O>[CH2:19]([O:21][C:22]([C:24]1[C:32]2[CH2:31][CH2:30][N:29]([C:14]3[CH:15]=[CH:16][C:11]([C:8]4([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18])[CH2:10][CH2:9]4)=[CH:12][CH:13]=3)[C:28](=[O:33])[C:27]=2[N:26]([C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)[N:25]=1)=[O:23])[CH3:20]

Komponenten

8

Edukt 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 22240468Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylateHCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

Produkt 1

HCID 69516007HCID 69516007, VerbindungAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Part A. [1-(4-Iodo-phenyl)-cyclopropyl]-carbamic acid tert-butyl ester (0.34 g, 0.95 mmol) and 1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.30 g, 0.97 mmol) were stirred in DMSO (1 mL). K2CO3 (0.25 g, 1.81 mmol), CuI (87 mg, 0.46 mmol) and 1,10-phenanthroline (83 mg, 0.46 mmol) were added. The resulting mixture was heated at 120° C. for 2.5 h. After cooling, it was extracted with EtOAc (2×), washed with H2O and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by FCC (silica gel, CH2Cl2:EtOAc=1:1, then EtOAc) to give 6-[4-(1-tert-butoxycarbonylamino-cyclopropyl)-phenyl]-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.24 g, yield: 46%).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionit was extracted with EtOAc (2×)
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by FCC (silica gel, CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-b2edc9aaa12f49dc9fbf5a3bd54c5f93
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312214B2

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