Dimethylformamide → 4-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3-methoxybenzonitrile

HRID 9217

Reaktionsgleichung

Reaktionsgleichung von HRID 9217
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([S:26][CH3:27])[C:16]([N:17]([CH2:22][CH:23]4[CH2:25][CH2:24]4)[CH2:18][CH:19]4[CH2:21][CH2:20]4)=[C:12]3[CH:11]=[CH:10][CH:9]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.C(OCC)(=O)C.[CH3:36][N:37](C)C=O>[C-]#N.[Zn+2].[C-]#N>[CH:19]1([CH2:18][N:17]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:16]2[C:15]([S:26][CH3:27])=[N:14][N:13]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([C:36]#[N:37])=[CH:3][C:4]=4[O:28][CH3:29])=[CH:9][CH:10]=[CH:11][C:12]=23)[CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 21984710N-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine

Produkt 1

HCID 219845664-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

After dissolving N-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine (60 mg) in N,N-dimethylformamide (0.26 mL), zinc cyanide (31 mg) and tetrakis (triphenylphosphine)palladium (0) complex (23 mg) were added, the mixture was heated and stirred at 95° C. for 12 hours and then cooled to room temperature, and ethyl acetate was added. After filtering out the precipitated insoluble portion, extraction was performed with ethyl acetate. The obtained organic layer was washed with water and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:8) to obtain the title compound (32 mg) as a yellow oil.

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperaturecooled to room temperature
  4. filtrationAfter filtering out
  5. extractionthe precipitated insoluble portion, extraction
  6. washThe obtained organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:8)

Quellen und Nachweise

ORD-Eintrag
ord-47a5528724e2431dbb12cb455458e194
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091215B2

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