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2-Bromopropane → 3-[4-(Benzyloxy)phenyl]-6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

HRID 573353
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 573353
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][C:20]([F:24])=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:26][NH2:27].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:35]([CH3:37])[CH3:36]>CC(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:17]3=[N:18][CH:19]=[C:20]([F:24])[CH:21]=[C:22]3[N:27]([CH:35]([CH3:37])[CH3:36])[N:26]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 24654Hydrazine hydrate (1:1)HCID 66727888[4-(Benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone

Produkt 1

HCID 667282723-[4-(Benzyloxy)phenyl]-6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of [4-(benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone (100 mg) and hydrazine hydrate (77 mg) in 2-propanol (5 mL) was stirred at room temperature for 30 min and at 90° C. for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in DMF (5 mL), and then Cs2CO3 (150 mg, 0.46 mmol) and 2-bromopropane (50.5 mg) were added successively. The mixture was stirred for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (70.0 mg).

Aufarbeitung

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in DMF (5 mL)
  5. stirringThe mixture was stirred for 12 h
  6. extractionextracted with AcOEt
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-06fe055b39794ab5aaf1dbe4da08b2ec
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029536B2

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