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Sodium Carbonate → 3-(4-(4-(7-Methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)benzonitrile

HRID 503539
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 503539
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[C:40]4[C:35](=[CH:36][C:37]([O:41][CH3:42])=[CH:38][N:39]=4)[N:34]=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)=[N:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:42][O:41][C:37]1[CH:36]=[C:35]2[C:40]([C:31]([O:30][C:27]3[CH:28]=[CH:29][C:24]([NH:23][C:16]4[C:17]5[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:13]([C:7]5[CH:8]=[C:3]([CH:4]=[CH:5][CH:6]=5)[C:1]#[N:2])=[N:14][N:15]=4)=[CH:25][CH:26]=3)=[CH:32][CH:33]=[N:34]2)=[N:39][CH:38]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 866286654-chloro-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine

Produkt 1

HCID 673179683-(4-(4-(7-Methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a nitrogen purged sealed tube, 1,4-dioxane (1.4 mL) was added and the tube was purged with nitrogen for 5 min and sealed. 3-Cyanophenylboronic acid (0.056 g, 0.384 mmol), 4-chloro-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine (0.150 g, 0.349 mmol), and 2.0 M sodium carbonate (0.349 mL, 0.698 mmol) were added to the tube, followed by 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.013 g, 0.017 mmol). The tube was purged with nitrogen, sealed, and the mixture was heated to 100° C. for 17 h. The mixture was allowed to cool to RT and was concentrated in vacuo. The crude material was purified by silica gel chromatography using 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2. The remaining impurities were removed by diluting the crude with methanol causing a light yellow solid to precipitate, which were filtered and air dried to yield 3-(4-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)benzonitrile. MS [M+H]=497.0; Calc'd 496.5 for C30H20N6O2.

Aufarbeitung

  1. customIn a nitrogen purged
  2. customsealed tube
  3. addition1,4-dioxane (1.4 mL) was added
  4. customthe tube was purged with nitrogen for 5 min
  5. customsealed
  6. customThe tube was purged with nitrogen
  7. customsealed
  8. temperatureto cool to RT
  9. concentrationwas concentrated in vacuo
  10. customThe crude material was purified by silica gel chromatography
  11. customThe remaining impurities were removed
  12. additionby diluting the crude with methanol causing a light yellow solid
  13. customto precipitate
  14. filtrationwhich were filtered
  15. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-7e108537eeca4a90a5f455b995e3c728
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07776857B2

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