Sodium Carbonate → 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl ester

HRID 1935281

Reaktionsgleichung

Reaktionsgleichung von HRID 1935281
[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[NH:19]1[C:27]2[C:22](=[CH:23][C:24](B(O)O)=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:24]2[CH:23]=[C:22]3[C:27](=[CH:26][CH:25]=2)[NH:19][CH:20]=[CH:21]3)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343615-Indolylboronic acidHCID 674834473-Cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester

Produkt 1

HCID 674852183-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl esterAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A slurry of dichlorobis(triphenylphosphine)palladium(II) (119 mg, 0.17 mmol) in 1,2-dimethoxyethane (10 mL) was treated with 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (1.00 g, 2.79 mmol). The reaction slurry was stirred at 25° C. for 10 min and then treated with a mixture of 5-indolylboronic acid (670 mg, 4.19 mmol) in water (5 mL) and a 2M aqueous sodium carbonate solution (2.8 mL, 5.58 mmol). The resulting reaction mixture was heated under reflux for 2 h. The reaction mixture was allowed to cool to 25° C. and then filtered to remove the catalyst. The filtrate was partitioned between water (50 mL) and methylene chloride (50 mL), and the layers were separated. The aqueous layer was further extracted with methylene chloride (50 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/2 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl ester (347 mg, 36%) as a light brown oil: EI-HRMS m/e calcd for C23H25NO2 (M+) 347.1885, found 347.1887.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 2 h
  4. temperatureto cool to 25° C.
  5. filtrationfiltered
  6. customto remove the catalyst
  7. customThe filtrate was partitioned between water (50 mL) and methylene chloride (50 mL)
  8. customthe layers were separated
  9. extractionThe aqueous layer was further extracted with methylene chloride (50 mL)
  10. dry with materialThe combined organic extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f5236949d3e94226b4c867a223d4a7c3
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384220B2

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