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Cesium carbonate → [5-(4H-Pyrazol-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

HRID 2068614
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2068614
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+].[NH:25]1[CH:29]=[C:28](B(O)O)[CH:27]=[N:26]1>COCCOC.O.C(OCC)(=O)C.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]>[N:25]1[N:26]=[CH:27][CH:28]([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:29]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 10796Cesium carbonateHCID 177502781H-Pyrazole-4-boronic acidHCID 86646712HCID 86646712, Verbindung

Produkt 1

HCID 44224461[5-(4H-Pyrazol-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanoneAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

cis-(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.15 mmol) was added to a solution of caesium carbonate (0.15 mmol), 4-pyrazoleboronic acid (0.3 mmol) and palladium tetrakis(triphenylphosphine) (0.03 mmol) in DME (6 mL), IMS (2 mL) and water (0.001 mL). The reaction mixture was heated by microwave irradiation to 140° C. for 20 minutes and then diluted with ethyl acetate (5 mL) and washed with water. The organic solution was dried and filtered and the solvent evaporated. The residue was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound as a pale yellow oil (10 mg). LCMS m/z 316.27 [M+H]+ RT=9.34 min. (Analytical Method 2).

Aufarbeitung

  1. washwashed with water
  2. customThe organic solution was dried
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by HPLC
  6. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-15450053dadb43349e5e0bfbe9f2667b
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299063B2

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