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Sodium Carbonate → 2-(4-Benzyloxy-5-ethyl-2-methoxy-phenyl)-6-(2,5-dimethyl-pyrrol-1-yl)-pyridine

HRID 392871
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 392871
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[N:3]=1.[CH2:15]([O:22][C:23]1[C:28]([CH2:29][CH3:30])=[CH:27][C:26](B(O)O)=[C:25]([O:34][CH3:35])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.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>[CH2:15]([O:22][C:23]1[C:28]([CH2:29][CH3:30])=[CH:27][C:26]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N:8]3[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]3[CH3:14])[N:3]=2)=[C:25]([O:34][CH3:35])[CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
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Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 155127672-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridineHCID 226621034-Benzyloxy-5-ethyl-2-methoxy-phenylboronic acid

Produkt 1

HCID 226620952-(4-Benzyloxy-5-ethyl-2-methoxy-phenyl)-6-(2,5-dimethyl-pyrrol-1-yl)-pyridineAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 5.00 g (19.91 mmol) of 2-bromo-6-(2,5-dimethylpyrrol-1-yl)pyridine, 5.98 g (20.91 mmol) of 4-benzyloxy-5-ethyl-2-methoxy-phenylboronic acid (5), 8.44 g (79.64 mmol) of sodium carbonate and 1.15 g (0.996 mmol) of tetrakis(triphenylphosphine)palladium(0) were combined in 90 mL of ethanol and 10 mL of water. The solution was allowed to reflux for 64 hours, and then the reaction mixture was concentrated in vacuo. The resultant yellow residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The aqueous layer was extracted again with ethyl acetate (200 mL). The combined organic extracts were washed with brine (1×200 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield crude product as a yellow oil which crystallized upon standing. Recrystallization of this solid from absolute ethanol afforded 6.00 g (73%) of 2-(4-benzyloxy-5-ethyl-2-methoxy-phenyl)-6-(2,5-dimethyl-pyrrol-1-yl)-pyridine (6) as a tan solid.

Aufarbeitung

  1. temperatureto reflux for 64 hours
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe resultant yellow residue was partitioned between ethyl acetate (200 mL) and water (200 mL)
  4. extractionThe aqueous layer was extracted again with ethyl acetate (200 mL)
  5. washThe combined organic extracts were washed with brine (1×200 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield crude product as a yellow oil which
  10. customcrystallized
  11. customRecrystallization of this solid from absolute ethanol

Quellen und Nachweise

ORD-Eintrag
ord-27d71911b317411e8157e7892752fd53
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06803470B2

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