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Potassium Carbonate → (1-(5-(4-Cyclopropylpyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

HRID 630549
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 630549
B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:25]1[CH:26]=[N:27][C:28]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([C:40]([N:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[O:41])[CH:38]=3)[C:33]([S:47][CH3:48])=[CH:32]2)=[N:29][CH:30]=1.Br[C:50]1[CH:55]=[C:54]([CH:56]2[CH2:58][CH2:57]2)[CH:53]=[CH:52][N:51]=1.C(=O)([O-])[O-].[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].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:56]1([C:54]2[CH:53]=[CH:52][N:51]=[C:50]([C:25]3[CH:30]=[N:29][C:28]([N:31]4[C:39]5[C:34](=[CH:35][CH:36]=[C:37]([C:40]([N:42]6[CH2:43][CH2:44][CH2:45][CH2:46]6)=[O:41])[CH:38]=5)[C:33]([S:47][CH3:48])=[CH:32]4)=[N:27][CH:26]=3)[CH:55]=2)[CH2:58][CH2:57]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 457879032-Bromo-4-cyclopropylpyridineHCID 118676809(1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

Produkt 1

HCID 118676890
(1-(5-(4-Cyclopropylpyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Bis(pinacolato)diboron (0.584 g, 2.3 mmol) and potassium acetate (0.421 g, 4.29 mmol) were added at room temperature to a solution of 341a) (0.6 g, 1.43 mmol) in dry dioxane (35 mL). The reaction apparatus was flushed with argon, PdCl2(dppf) (58 mg, 0.071 mmol) was added and the resulting mixture was stirred for 1 h at 110° C. (complete consumption of starting material). 2-bromo-4-cyclopropyl-pyridine (0.328 g, 2.14 mmol), potassium carbonate (2M, 2.5 mL) and tetrakis(triphenylphosphine)palladium(0) (83 mg, 0.071 mmol) were added successively and the reaction mixture was stirred for 16 h at 100° C. The mixture was then cooled to ambient temperature and filtered through a sintered funnel. The filtrate was concentrated and the remnant was purified by flash column chromatography [silica; dichloromethane with 2% methanol]. White solid. Yield: 0.28 g (43% of theory)

Aufarbeitung

  1. additionwas added
  2. custom(complete consumption of starting material)
  3. stirringthe reaction mixture was stirred for 16 h at 100° C
  4. temperatureThe mixture was then cooled to ambient temperature
  5. filtrationfiltered through a sintered funnel
  6. concentrationThe filtrate was concentrated
  7. customthe remnant was purified by flash column chromatography [silica; dichloromethane with 2% methanol]

Quellen und Nachweise

ORD-Eintrag
ord-ae184684a3454d3cb839a24f4e366ad9
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315490B2

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