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

Cesium carbonate → {4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester

HRID 2068620
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2068620
Br[C:2]1[S:6][CH:5]=[C:4]([C:7]([N:9]2[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:25]([O:27][C:28](=[O:44])[CH2:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1)[CH3:26]>COCCOC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH2:25]([O:27][C:28](=[O:44])[CH2:29][N:30]1[CH:34]=[C:33]([C:2]2[S:6][CH:5]=[C:4]([C:7]([N:9]3[CH:18]4[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]4)[CH2:12][CH2:11][CH2:10]3)=[O:8])[CH:3]=2)[CH:32]=[N:31]1)[CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 162183851-(Ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid pinacol esterHCID 86646712HCID 86646712, Verbindung

Produkt 1

HCID 58110350{4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-pyrazol-1-yl}-acetic acid ethyl esterAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.217 g, 0.66 mmol) was added to a solution of caesium carbonate (0.32 g, 0.99 mmol), [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]acetic acid ethyl ester (0.203 g, 0.725 mmol) and palladium tetrakis(triphenylphosphine) (76 mg, 0.07 mmol) in DME (6 mL), IMS (2 mL) and water (1 mL). The reaction mixture was purged with nitrogen and heated by microwave irradiation to 140° C. for 20 minutes then diluted with water and extracted with DCM (×2). The organic solution was dried over sodium sulfate, filtered and the solvent evaporated. The crude material was purified by chromatography on a 5 g silica II cartridge, eluting with 10-50% ethyl acetate in cyclohexane then columned using 0-25% diethyl ether in DCM to afford {4-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester (164 mg). LCMS m/z 402.41 [M+H]+ R.T.=3.91 min (Analytical Method 6).

Aufarbeitung

  1. customThe reaction mixture was purged with nitrogen
  2. additionthen diluted with water
  3. extractionextracted with DCM (×2)
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe crude material was purified by chromatography on a 5 g silica II cartridge
  8. washeluting with 10-50% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-7fb9ff7274bb4d139f77a0efd216299c
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299063B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion