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Tetrahydrofuran → 5-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1820894
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1820894
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.N1C2C(=CC=CN=2)C=C1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].O1CCCC1>C(=O)([O-])[O-].[K+].[K+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([C:2]2[CH:3]=[C:4]3[CH:5]=[CH:6][NH:7][C:8]3=[N:9][CH:10]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 27347023,4-Dimethoxyphenylboronic acidHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 101492305-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 11430Potassium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a microwave safe tube, 5-bromo-7-azaindole (81, 392 mg, 1.99 mmol), prepared from 7-azaindole following the published procedure (Marie-Claude, Viaud, Heterocycles, 1999, 50, 1065-1080), 3,4-dimethoxyphenyl boronic acid (905 mg, 4.97 mmol), and tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.099 mol) were mixed in 1.0 M of potassium carbonate (6.0 mL) and tetrahydrofuran (9.5 mL, 0.12 mol). The resulting mixture was heated at 120° C. in a CEM Discover microwave unit for 10 minutes. Ethyl acetate and water were added, and the two layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded the crude material, which was purified by column chromatography (40-70% ethyl acetate:hexanes) to yield the desired product as a light yellow solid (82, 207 mg, 41%). MS(ESI) [M+H+]+=255.2.

Aufarbeitung

  1. customthe two layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure
  6. customafforded the crude material, which
  7. customwas purified by column chromatography (40-70% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-755c5fc7ffa141e29eaaabaa825a9ce4
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07605168B2

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