StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Cesium carbonate → tert-Butyl 4-(5-(thiophen-2-yl)imidazo[1,2-a]pyrazin-8-yl)piperazine-1-carboxylate

HRID 1045751
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1045751
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:4][CH:3]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 27339602-Thiopheneboronic acidHCID 10249304tert-Butyl 4-(5-bromoimidazo[1,2-a]pyrazin-8-yl)piperazine-1-carboxylate

Produkt 1

HCID 58447036tert-Butyl 4-(5-(thiophen-2-yl)imidazo[1,2-a]pyrazin-8-yl)piperazine-1-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A 100 mL round bottom flask was charged with tert-butyl 4-(5-bromoimidazo[1,2-a]pyrazin-8-yl)piperazine-1-carboxylate (1.0 g, 2.62 mmol), thiophen-2-ylboronic acid (0.50 g, 3.93 mmol), Pd(PPh3)2Cl2 (200 mg, 0.26 mmol), Cs2CO3 (0.60 g, 3.93 mmol) and DMF (30 mL). After air was purged by bubbling N2 into the reaction solution, the reaction mixture was heated at 90° C. for 30 h. Work-up: the reaction mixture was poured into water (150 mL) and extracted with EtOAc (200 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether, to afford 0.70 g (72%) of the product as a yellow solid. MS m/z: 386 (M+H+).

Aufarbeitung

  1. customAfter air was purged
  2. customby bubbling N2 into the reaction solution
  3. additionthe reaction mixture was poured into water (150 mL)
  4. extractionextracted with EtOAc (200 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-9249a64c31e341b9bacb3f4686670980
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08569300B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion