2-Iodoxybenzoic acid → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanone

HRID 456158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456158
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[N:17]=[CH:16]4)[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:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[N:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 1087942-Iodoxybenzoic acidHCID 58190458(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanol

Produkt 1

HCID 58190472(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanoneAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A suspension of (6-chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanol (500.0 mg, 1.60 mmol) and 2-Iodoxybenzoic acid (45% pure, 1488.0 mg, 2.39 mmol) in 10 mL acetone was heated at refluxe and stirred for 3 hours. Solvent was removed under reduced pressure. The residue was diluted with water, and the pH value of the solution adjusted to around 10 with 10% aqueous NaOH. The precipitates were collected by filtration and washed with water three times. The solid was dissolved in DCM, dried over Na2SO4, filtered and concentrated to give the title compound as a white solid (410.0 mg, 78%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.46 (s, 1H), 8.42 (m, 1H), 8.32 (m, 1H), 8.27 (d, 1H), 7.95 (dd, 1H), 7.815 (d, 1H), 7.66 (d, 1H), 4.12 (s, 2H). LCMS (method A): [MH]+=312, tR=4.64 min.

Aufarbeitung

  1. temperaturewas heated at refluxe
  2. customSolvent was removed under reduced pressure
  3. additionThe residue was diluted with water
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water three times
  6. dissolutionThe solid was dissolved in DCM
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-97cf965344844d9eae374bece554567a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

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