Potassium Carbonate → 8-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 512829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512829
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1.C([O-])([O-])=O.[K+].[K+]>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>[CH3:18][N:19]1[CH:23]=[C:22]([C:2]2[N:7]=[N:6][C:5]([N:8]3[CH2:17][CH2:16][C:11]4([O:15][CH2:14][CH2:13][O:12]4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:21]=[N:20]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 32267178-(6-Chloropyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Produkt 1

HCID 896143308-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a two-neck flask was placed 8-(6-chloropyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane, prepared as in STEP 1 above (3.07 g, 12 mmol), 1-methylpyrazole-4-boronic acid pinacol ester (3.24 g, 15.6 mmol), K2CO3 (6.62 g, 48 mmol), and Pd(PPh3)4 (693 mg, 0.6 mmol). The resulting mixture was degassed and refilled with N2 (3 times). 1,4-Dioxane/H2O (15 mL/5 mL) was added and the resulting mixture was heated at 100° C. for 4 h. The resulting mixture was then poured into EtOAc/H2O (100 mL/100 mL). The organic layer was washed with brine (100 mL), dried (Na2SO4), and filtered. The solvent was removed by roto-evaporator and the resulting residue purified by column using EtOAc as the eluent to yield 8-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane.

Aufarbeitung

  1. customIn a two-neck flask was placed
  2. customThe resulting mixture was degassed
  3. additionrefilled with N2 (3 times)
  4. addition1,4-Dioxane/H2O (15 mL/5 mL) was added
  5. additionThe resulting mixture was then poured into EtOAc/H2O (100 mL/100 mL)
  6. washThe organic layer was washed with brine (100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe solvent was removed by roto-evaporator
  10. customthe resulting residue purified by column

Quellen und Nachweise

ORD-Eintrag
ord-1fd20e3362bb4862a162d577ee417953
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102669B2

Notizen zur Reaktion

Wird geladen…