Sodium Carbonate → (z)-1,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylene]-2h-indol-2-one

HRID 382064

Reaktionsgleichung

Reaktionsgleichung von HRID 382064
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](B(O)O)[CH:8]=2)[CH:3]=[CH:2]1.I[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1/[C:16](=[CH:24]/[C:25]1[NH:26][CH:27]=[CH:28][C:29]=1[O:30][CH3:31])/[C:17](=[O:23])[NH:18]2.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3/[C:16](=[CH:24]/[C:25]3[NH:26][CH:27]=[CH:28][C:29]=3[O:30][CH3:31])/[C:17](=[O:23])[NH:18]4)[CH:8]=2)[CH:3]=[CH:2]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27632051H-Indol-6-ylboronic acidHCID 15548053(Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×

Produkt 1

HCID 9841570(z)-1,3-Dihydro-4-(6-indolyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylene]-2h-indol-2-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 6-indoleboronic acid (36 mg, 0.22 mmol) (from Step A above), (Z)-1,3-dihydro-4-iodo-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-indol-2-one (54 mg, 0.15 mmol) (Starting Material 3) and sodium carbonate (52 mg, 0.49 mmol) in 5 mL DME and 2.5 mL water was degassed for 15 min. by bubbling argon through the solution. Dichlorobis(triphenylphosphine)palladium (II) (10 mol %) (Aldrich) was then added and the reaction was heated at 90° C. for 2 days. The reaction was then poured into 100 mL water and the product was extracted with ethyl acetate (4×50 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The resulting product, (Z)-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one), was purified via flash column chromatography (40% EtOAc/hex) to yield 33 mg (62%) orange powder.

Aufarbeitung

  1. customby bubbling argon through the solution
  2. additionDichlorobis(triphenylphosphine)palladium (II) (10 mol %) (Aldrich) was then added
  3. additionThe reaction was then poured into 100 mL water
  4. extractionthe product was extracted with ethyl acetate (4×50 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting product, (Z)-1,3-dihydro-4-(6-indolyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one), was purified via flash column chromatography (40% EtOAc/hex)

Quellen und Nachweise

ORD-Eintrag
ord-35ebf44b134347d5b0c196889662e998
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307056B1

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