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1,4-Dioxane → HCID 66692086, Verbindung

HRID 520595
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 520595
Br[C:2]1[CH:3]=[C:4]([NH2:12])[C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9]=2[CH:10]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:23]2[C:27]3=[N:28][CH:29]=[CH:30][C:31](B(O)O)=[C:26]3[CH:25]=[CH:24]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:11][N:8]1[C:9]2[CH:10]=[C:2]([C:31]3[CH:30]=[CH:29][N:28]=[C:27]4[N:23]([S:20]([C:17]5[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=5)(=[O:21])=[O:22])[CH:24]=[CH:25][C:26]=34)[CH:3]=[C:4]([NH2:12])[C:5]=2[CH:6]=[N:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 582557716-Bromo-1-methyl-1h-indazol-4-amineHCID 68226575HCID 68226575, Verbindung

Produkt 1

HCID 66692086HCID 66692086, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6-Bromo-1-methyl-1H-indazol-4-amine (300 mg), {1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}boronic acid (482 mg), tripotassium phosphate (845 mg) and Pd(dppf)Cl2 (97 mg) were added to 1,4-dioxane (7 ml) and water (3.5 ml). The reaction mixture was heated in the microwave at 100° C. for 15 min. After this time the reaction mixture was partitioned between water (20 ml) and DCM (20 ml). The organic layer was extracted then put through hydrophobic frits. The solvent was removed to afford a crude mixture. The residue was purified by column chromatography on silica (100 g) eluting with a gradient of 0-100% ethyl acetate:cyclohexane. Fractions containing desired product were combined and concentrated in vacuo to afford the title compound, 312 mg as an orange solid.

Aufarbeitung

  1. customAfter this time the reaction mixture was partitioned between water (20 ml) and DCM (20 ml)
  2. extractionThe organic layer was extracted
  3. customThe solvent was removed
  4. customto afford a crude mixture
  5. customThe residue was purified by column chromatography on silica (100 g)
  6. washeluting with a gradient of 0-100% ethyl acetate
  7. additionFractions containing desired product
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d67037304fcc41e29a75369236f251f1
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09326987B2

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