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Diethyl Ether → 5-Pyridin-4-yl-thiophene-3-carboxylic acid ethyl ester

HRID 1914552
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1914552
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9](Br)[S:8][CH:7]=1)=[O:5])[CH3:2].[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOCC>O.COCCOC>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)[S:8][CH:7]=1)=[O:5])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 15293216Ethyl 5-bromothiophene-3-carboxylate

Produkt 1

HCID 581102865-Pyridin-4-yl-thiophene-3-carboxylic acid ethyl esterAusbeute 2,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
2×
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

5-Bromo-thiophene-3-carboxylic acid ethyl ester (5.26 mmol), 4-pyridylboronic acid (5.26 mmol), caesium carbonate (7.9 mmol) and palladium (0) tetrakis-triphenylphosphine (0.53 mmol) were dissolved in a mixture of water (10 mL), IMS (20 mL) and DME (50 mL). The reaction mixture was heated by microwave irradiation to 140° C. for 10 minutes, and then ether (100 mL) and water (20 mL) were added. The organic solution was washed with water, dried with anhydrous magnesium sulfate, filtered and the solvent evaporated to give brown oil. The residue was purified by flash chromatography on silica. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.035 g) as an off-white solid. LCMS m/z 234.04 [M+H]+ R.T.=2.10 min. (Analytical Method 5).

Aufarbeitung

  1. washThe organic solution was washed with water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customto give brown oil
  6. customThe residue was purified by flash chromatography on silica
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-12ce94c540f24bc79b3d7d16fd6233ea
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08614209B2

Notizen zur Reaktion

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