Potassium Carbonate → 1-methyl-5-phenyl-3-(pyrrolidin-1-yl)-1H-pyrazolo[3,4-c]pyridazin-4-ol

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Reaktionsgleichung

I[C:2]1[C:10]2[C:9]([OH:11])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:7]=[N:6][C:5]=2[N:4]([CH3:18])[N:3]=1.[NH:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu](I)I>[CH3:18][N:4]1[C:5]2[N:6]=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:9]([OH:11])[C:10]=2[C:2]([N:19]2[CH2:26][CH2:25][CH2:24][CH2:20]2)=[N:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 3-iodo-1-methyl-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-4-ol (100 mg, 0.28 mmol), copper iodide (11 mg, 0.056 mmol), L-proline (13 mg, 0.11 mmol), K2CO3 (193 mmol, 1.4 mmol) in anhydrous DMF (5.6 mL) was degassed by bubbling nitrogen through for 10 minutes, then heated to 110° C. for 20 h. The mixture was left to cool to room temperature, then partitioned between ethyl acetate and water, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried (MgSO4), filtered and evaporated. The residue (117 mg) was used as such in the next step.

Aufarbeitung

customwas degassed
customby bubbling nitrogen through for 10 minutes
waitThe mixture was left
temperatureto cool to room temperature
custompartitioned between ethyl acetate and water
extractionthe aqueous phase was extracted with ethyl acetate
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-a54633765b9b41599789323cf311899a
Quelldatensatz: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09371332B2

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