Sodium Carbonate → N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

HRID 227798

Reaktionsgleichung

Reaktionsgleichung von HRID 227798
F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F:19][C:20]1[CH:25]=[C:24](B(O)O)[CH:23]=[CH:22][N:21]=1.[Br:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][C:35]=1[O:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:47]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[N:46][N:45]=2)=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[F:19][C:20]1[CH:25]=[C:24]([C:34]2[CH:33]=[N:32][CH:31]=[CH:30][C:35]=2[O:36][C:37]2[CH:38]=[CH:39][C:40]([NH:43][C:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:47]([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)=[N:46][N:45]=3)=[CH:41][CH:42]=2)[CH:23]=[CH:22][N:21]=1.[Br:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][C:35]=1[O:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:47]([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)=[N:46][N:45]=2)=[CH:39][CH:38]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 27833962-Fluoropyridine-4-boronic acidHCID 66731439N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

Produkt 2

HCID 66731439N-(4-(3-bromopyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amineHCID 66732281N-(4-(3-(2-fluoropyridin-4-yl)pyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A resealable reaction tube was charged with tri-tert-butylphosphonium tetrafluoroborate (0.024 g, 0.082 mmol), palladium (II) acetate (0.009 g, 0.041 mmol), 2-fluoropyridine4-boronic acid (0.086 g, 0.614 mmol) and N-(4-(3-bromopyridin4-yloxy)phenyl)-4-phenylphthalazin-1-amine (0.192 mg, 0.409 mmol) and was purged with nitrogen for several minutes. 1.2 mL of dioxane and 2.0 M aqueous sodium carbonate (0.614 mL, 0.123 mmol) were added, the tube was sealed, and the reaction mixture was heated to 100° C. for 48 h. The mixture was diluted with EtOAc and washed with water. The organic portion was dried with MgSO4 and concentrated. Purification by Gilson reverse phase liquid chromatography (5-70% ACN/water/0.1% TFA over 14 min) provided N-(4-(3-(2-fluoropyridin-4-yl)pyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine as a mixture with the hydrodehalogenation product of N-(4-(3-bromopyridin-4-yloxy)phenyl)4-phenylphthalazin-1-amine.

Aufarbeitung

  1. customwas purged with nitrogen for several minutes
  2. customthe tube was sealed
  3. washwashed with water
  4. dry with materialThe organic portion was dried with MgSO4
  5. concentrationconcentrated
  6. customPurification by Gilson reverse phase liquid chromatography (5-70% ACN/water/0.1% TFA over 14 min)

Quellen und Nachweise

ORD-Eintrag
ord-bfaff0fbea714597b399ff08fb409554
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560551B2

Verknüpfte Notizen

Wird geladen…