Sodium Carbonate → 1-(1-Methylethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridine

HRID 573290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573290
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1[O:11][C:12]1[CH:17]=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14][CH:13]=1.Br[C:28]1[C:32]2=[N:33][CH:34]=[CH:35][CH:36]=[C:31]2[N:30]([CH:37]([CH3:39])[CH3:38])[N:29]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[CH3:39][CH:37]([N:30]1[C:31]2[C:32](=[N:33][CH:34]=[CH:35][CH:36]=2)[C:28]([C:15]2[CH:14]=[CH:13][C:12]([O:11][C:3]3[N:2]([CH3:1])[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:5]4[N:4]=3)=[CH:17][CH:16]=2)=[N:29]1)[CH3:38]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 667280773-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridineHCID 866889663-Methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-3H-imidazo[4,5-b]pyridine

Produkt 1

HCID 866889671-(1-Methylethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridineAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

A mixture of 3-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-3H-imidazo[4,5-b]pyridine (215 mg), 3-bromo-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine (147 mg), Pd(PPh3)4 (21 mg) and Na2CO3 (227 mg) in DME (5 mL) and water (1 mL) was refluxed overnight under Ar atmosphere. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) and recrystallized from AcOEt/hexane to give the title compound (225 mg).

Aufarbeitung

  1. temperaturewas refluxed overnight under Ar atmosphere
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
  7. customrecrystallized from AcOEt/hexane

Quellen und Nachweise

ORD-Eintrag
ord-7eecf4bab6ae4b5ba770a0d51cb2f0e3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029536B2

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