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Cesium carbonate → 2,2-dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 547475
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 547475
N1C2[C:4](=[CH:5]C=CC=2)[C:3]([C:10]2[N:11]=[C:12]3[C:18]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][N:16](COCC[Si](C)(C)C)[C:13]3=[N:14][CH:15]=2)=C1.C(=O)([O-])[O-].[Cs+].[Cs+].[H-].[Na+].[H][H]>C(#N)C.C1(C)C=CC=CC=1.CC(C)=O>[CH3:22][C:20]([CH3:21])([CH3:23])[C:19]([C:18]1[C:12]2[C:13](=[N:14][CH:15]=[C:10]([C:3]3[CH:3]=[CH:10][N:11]=[C:5]([N:16]4[CH2:17][CH2:18][CH2:12][CH2:13]4)[CH:4]=3)[N:11]=2)[NH:16][CH:17]=1)=[O:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 24758Sodium hydrideHCID 578295791-[2-(1H-indol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 441923402,2-dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one
Ausbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 20247278Toluene acetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Step 2—A mixture of 1-[2-(1H-indol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.2 g, 0.446 mmol), 1 (0.23 g, 0.892 mmol), and cesium carbonate (0.29 g, 0.892 mmol) in 4 mL of acetonitrile was stirred at 80° C. overnight. TLC (hexanes/EtOAc 7/3) showed little conversion, so NaH 60% dispersion in oil (0.067 g, 1.672 mmol) was added and the after hydrogen evolution had stopped the reaction mixture was stirred at 130° C. under microwave irradiation for two hours before being cooled to RT. The reaction mixture was partitioned between EtOAc and saturated aqueous ammonium chloride, the aqueous layer was back extracted twice with EtOAc. Combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc) and then a second time (toluene/acetone 0-10% acetone) to give 0.028 g of 2 (10% yield)

Aufarbeitung

  1. additionwas added
  2. stirringwas stirred at 130° C. under microwave irradiation for two hours
  3. temperaturebefore being cooled to RT
  4. customThe reaction mixture was partitioned between EtOAc and saturated aqueous ammonium chloride
  5. extractionthe aqueous layer was back extracted twice with EtOAc
  6. dry with materialCombined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-14631894312147b48cd97ad5a63875b6
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07939531B2

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