Cesium carbonate → 3-(6-Methoxypyridin-3-yl)-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

HRID 573327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573327
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH:11]([CH3:13])[CH3:12])[N:3]=1.[CH3:14][O:15][C:16]1[N:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][O:15][C:16]1[N:21]=[CH:20][C:19]([C:2]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[N:4]([CH:11]([CH3:13])[CH3:12])[N:3]=2)=[CH:18][CH:17]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 667280773-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine

Produkt 1

HCID 866889833-(6-Methoxypyridin-3-yl)-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridineAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 3-bromo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine (100 mg), 6-methoxypyridin-3-ylboronic acid (96 mg), Pd(OAc)2 (9.35 mg), and Xphos (39.7 mg) in THF (3 mL) was added a solution of Cs2CO3 (271 mg) in H2O (1 mL). The mixture was exposed to microwave irradiation at 100° C. for 30 min, 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 (100 mg).

Aufarbeitung

  1. customirradiation at 100° C. for 30 min
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c29caf5e70834c1f875e77dac3301b47
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029536B2

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