2-Iodoxybenzoic acid → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanone

HRID 69216

Reaktionsgleichung

Reaktionsgleichung von HRID 69216
[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:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH: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:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 1087942-Iodoxybenzoic acidHCID 58147515(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanol

Produkt 1

HCID 58147533(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(7-fluoro-quinolin-6-yl)-methanol (Stage 174.3, 329 g, 1.0 mmol) was dissolved in acetone (40 mL) and 2-iodoxybenzoic acid (45%, 1.245 g, 2.0 mmol) was added. The RM was heated to reflux for 3 h (suspension). The acetone was then removed under reduced pressure and the residue was taken up with water and 2 M NaOH. The beige suspension was filtered, washed with water and dried overnight under vacuum to afford the title compound as a beige powder (tR 4.31 min (conditions 3), MH+=327, 1H-NMR in DMSO-d6: 9.03 (d, 1H); 8.53 (d, 1H); 8.49-8.41 (m, 2H); 8.39 (s, 1H); 7.90 (d, 1H); 7.74 (d, 1H); 7.62 (dd, 1H)).

Aufarbeitung

  1. temperatureThe RM was heated
  2. temperatureto reflux for 3 h (suspension)
  3. customThe acetone was then removed under reduced pressure
  4. filtrationThe beige suspension was filtered
  5. washwashed with water
  6. customdried overnight under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a56559ab0f4c41dba0ca430dccd310b7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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