Cesium carbonate → HCID 57509990, Verbindung

HRID 624155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624155
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:18]3[CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19]3)=[O:17])=[CH:11][CH:10]=2)O1.Cl[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[NH:31][N:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.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]>[O:39]=[C:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([N:18]3[CH2:19][C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:26]3)=[O:17])=[CH:13][CH:14]=2)=[N:30][NH:31]1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 27751424-chlorophthalazin-1(2H)-oneHCID 68754457HCID 68754457, Verbindung

Produkt 1

HCID 57509990HCID 57509990, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

105 mg N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isoindoline-2-carboxamide (0.288 mmol) and 53 mg 4-chloro-1,2-dihydrophthalazin-1-one (0.288 mmol) were dissolved in 2.5 ml dioxane. Cesium carbonate (474 mg, 1.44 mmol) was dissolved in 0.25 ml water and the resulting solution added to the reaction mixture. After the addition of 27.8 mg [1,1′-bis(diphenylphosphino)-ferrocene]dichlorpalladium(II) (0.038 mmol) the reaction mixture was flushed with nitrogen and stirred for 30 minutes in the microwave (Biotage Initiator 2.5) at 110° C. Dioxane was removed under reduced pressure, water and dichloromethane added to the residue and the formed precipitation was filtered. After dissolving the solid matter in a larger amount of dichloromethane/methanol 8:2, silica gel was added and subsequently the solvent was removed under reduced pressure. This residue was was purified by column chromatography using dichloromethane/methanol 95:5. 1H NMR (DMSO-d6, 400 MHz): 6 ppm 12.73 (s, 1H), 8.55 (s, 1H), 8.33 (dd, 1H), 7.85-7.92 (m, 2H), 7.73-7.78 (m, 3H), 7.48 (d, 2H), 7.35-7.38 (m, 2H), 7.30-7.33 (m, 2H), 4.81 (s, 4H). MS (ESI(−)) m/e 383.2 (M+H)+.

Aufarbeitung

  1. additionthe resulting solution added to the reaction mixture
  2. customwas flushed with nitrogen
  3. customDioxane was removed under reduced pressure, water and dichloromethane
  4. additionadded to the residue
  5. customthe formed precipitation
  6. filtrationwas filtered
  7. dissolutionAfter dissolving the solid matter in a larger amount of dichloromethane/methanol 8:2, silica gel
  8. additionwas added
  9. customsubsequently the solvent was removed under reduced pressure
  10. customThis residue was was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a003cbd2afd243068fe6ab2a80e2c285
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302989B2

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