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2-Iodoxybenzoic acid → (6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanone

HRID 69242
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 69242
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:21]=[CH:20][C:19]4[C:15](=[CH:16][N:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]=4)[CH:14]=3)[OH:12])=[CH:9][N:10]=2)[N:7]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:21]=[CH:20][C:19]4[C:15](=[CH:16][N:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]=4)[CH:14]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 1087942-Iodoxybenzoic acidHCID 87523362(Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanol

Produkt 1

HCID 87523378(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-methanol (Stage 195.4, 580 mg, 1.349 mmol) was dissolved in acetone (40 mL) and heated 1 h to reflux together with 2-iodoxybenzoic acid (1.133 g, 4.05 mmol). The RM was cooled down to rt and the acetone was removed under reduced pressure. The residue was mixed with 2 M NaOH solution and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=50:50->0: 100) to afford the title compound as a light brown foam (tR 7.11 min (conditions 3), MH+=428).

Aufarbeitung

  1. temperatureheated 1 h
  2. customthe acetone was removed under reduced pressure
  3. additionThe residue was mixed with 2 M NaOH solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=50:50->0: 100)

Quellen und Nachweise

ORD-Eintrag
ord-31302cce90154816ad01c97c5ad7d61b
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822468B2

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