1,4-Dioxane → HCID 86667837, Verbindung

HRID 1913231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913231
[CH3:1][Si:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:8]1[N:13]2[N:14]=[CH:15][C:16](I)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]2)[CH:9]=1.[Cl:40][C:41]1[N:46]=[CH:45][C:44](B2OC(C)(C)C(C)(C)O2)=[CH:43][CH:42]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>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>[CH3:1][Si:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:44]3[CH:45]=[N:46][C:41]([Cl:40])=[CH:42][CH:43]=3)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]2)[CH:9]=1

Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27947192-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 66733407Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

Produkt 1

HCID 86667837HCID 86667837, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a 10-20 mL microwave flask was added ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (Int-5l, 1.41 g, 2.05 mmol), 6-chloropyridine-3-boronic acid pinacol ester (514 mg, 2.15 mmol), K3PO4 (1.31 g, 6.15 mmol), PdCl2(dppf).CH2O2 (167 mg, 0.21 mmol) and 9:1 1,4-dioxane:H2O (10 mL). The flask was flushed with argon and sealed. The reaction was stirred overnight at 100° C. After 18 hours, the reaction was diluted with DCM and washed with H2O. The aqueous was extracted with DCM (x2) and the combined organic layers were dried over Na2SO4. The solvent was reduced in vacuo and the title compound was purified via silica gel chromatography.

Aufarbeitung

  1. customThe flask was flushed with argon
  2. customsealed
  3. waitAfter 18 hours
  4. additionthe reaction was diluted with DCM
  5. washwashed with H2O
  6. extractionThe aqueous was extracted with DCM (x2)
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. customthe title compound was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3b158308c897475fbfc97fc64634885f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609675B2

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