Water → 4-{4-Chloro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile

HRID 1625262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625262
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C:14]2[NH:15][CH:16]=[CH:17][C:18](=O)[C:13]=2[C:12]([C:20]([F:23])([F:22])[F:21])=[N:11]1)[C:5]#[N:6].S(Cl)([Cl:26])=O.CN(C=O)C.O>C(Cl)(Cl)Cl>[Cl:26][C:18]1[CH:17]=[CH:16][N:15]=[C:14]2[N:10]([C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[CH3:1])[N:11]=[C:12]([C:20]([F:23])([F:22])[F:21])[C:13]=12

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1363901483-Methyl-4-{4-oxo-3-(trifluoromethyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile

Produkt 1

HCID 675025754-{4-Chloro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Compound (154d) (2.20 g) was dissolved in chloroform (14 mL), and thionyl chloride (1.00 mL) and DMF (0.148 mL) were added to the resulting solution, followed by reflux for 3 hr. Water was added to the reaction solution for distribution. The organic layer was washed with saturated sodium bicarbonate water. The organic layer after the washing was dried over anhydrous sodium sulfate, and the solvent was distilled away. 2-Propanol was added to the residue, and the precipitate was collected by filtration and then dried under reduced pressure to obtain compound (154e) (1.60 g, 71%).

Aufarbeitung

  1. temperatureby reflux for 3 hr
  2. washThe organic layer was washed with saturated sodium bicarbonate water
  3. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. addition2-Propanol was added to the residue
  6. filtrationthe precipitate was collected by filtration
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9fb95e0ba18d426b94cef799dd3431f8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779142B2

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