Ethyl Acetate → 7-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

HRID 347832

Reaktionsgleichung

Reaktionsgleichung von HRID 347832
Br[C:2]1[N:7]2[N:8]=[C:9]([CH2:14][CH3:15])[C:10]([N+:11]([O-:13])=[O:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[C:22]([CH2:24][O:25][CH3:26])[CH:21]=[C:20]([O:27][CH3:28])[C:19]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(OCC)(=O)C>COCCOC.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>[CH3:28][O:27][C:20]1[CH:21]=[C:22]([CH2:24][O:25][CH3:26])[CH:23]=[C:18]([O:17][CH3:16])[C:19]=1[C:2]1[N:7]2[N:8]=[C:9]([CH2:14][CH3:15])[C:10]([N+:11]([O-:13])=[O:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 17749109Barium hydroxide, octahydrateHCID 219844817-Bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridineHCID 230809452,6-Dimethoxy-4-methoxymethylphenylboric acid

Produkt 1

HCID 210841097-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-3-nitropyrazolo[1,5-a]pyridineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 7-bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (1.0 g) dissolved in a mixture of 1,2-dimethoxyethane (50 mL) and water (25 mL) was added 2,6-dimethoxy-4-(methoxymethyl)phenylboric acid (1.26 g), tetrakis(triphenylphosphine)palladium(0) (0.64 g) and barium hydroxide octahydrate (1.75 g), and the reaction mixture was heated and stirred for 2 hours at 80° C. To the resultant reaction mixture was added water and ethyl acetate, and remove insoluble residue was filtered out with celite. The filtrate was extracted with ethyl acetate, the organic extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography and the title compound (0.77 g) was obtained as yellow crystals from the n-hexane:ethyl acetate (3:1) fraction.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. customTo the resultant reaction mixture
  3. customremove insoluble residue
  4. filtrationwas filtered out with celite
  5. extractionThe filtrate was extracted with ethyl acetate
  6. extractionthe organic extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-165db9f6cc6a4469ad9e6eb4c7ef7aeb
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176216B2

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