1,10-Phenanthroline → 1-{6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinyl}-5-methyl-2-pyrrolidinone

HRID 222735

Reaktionsgleichung

Reaktionsgleichung von HRID 222735
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[CH:22]=[CH:21][C:20](I)=[CH:19][N:18]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH3:38][CH:39]1[NH:43][C:42](=[O:44])[CH2:41][CH2:40]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[N:18]=[CH:19][C:20]([N:43]5[CH:39]([CH3:38])[CH2:40][CH2:41][C:42]5=[O:44])=[CH:21][CH:22]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 660555-Methyl-2-pyrrolidoneHCID 574402941H-3-Benzazepine, 3-cyclobutyl-2,3,4,5-tetrahydro-7-[(5-iodo-2-pyridinyl)oxy]-

Produkt 1

HCID 104305641-{6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinyl}-5-methyl-2-pyrrolidinoneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
175 °C

Versuchsvorschrift

3-Cyclobutyl-7-[(5-iodo-2-pyridinyl)oxy]-2,3,4,5-tetrahydro-1H-3-benzazepine (E207) (294 mg, 0.7 mmol) 1,10 phenanthroline (38 mg, 0.2 mmol), 5-methyl-2-pyrrolidinone (139 mg 1.4 mmol) were dissolved in dioxane (2 ml). Copper(I) Iodide (39 mg, 0.2 mmol) and caesium carbonate (479 mg, 1.5 mmol) were added and the mixture heated in a microwave reactor at 175° C. for 15 minutes. The mixture was cooled and filtered through celite, washing through with dichloromethane. The filtrate was concentrated in vacuo and the crude material purified by column chromatography, eluting with dichloromethane through to a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90) to afford the title compound (137 mg); MS (ES+) m/e 392 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washwashing through with dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude material purified by column chromatography
  6. washeluting with dichloromethane through to a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90)

Quellen und Nachweise

ORD-Eintrag
ord-3c0b5f00e5b047a28b1d01e07da96d6f
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207331B2

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