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

HRID 1892320Notes

Reaction equation

HRID 1892320 reaction equation
[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>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

Participants

3

Reactant 1

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

Product 1

HCID 58147533(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-(7-fluoro-quinolin-6-yl)-methanol (1.8 g, 5.48 mmol) in acetone (200 mL) was added IBX (8.52 g, 45%, 13.69 mmol). The reaction mixture was stirred at reflux for 1 day. Then the solvent was removed under reduced pressure and the residue was dissolved in 200 mL of water. The solution was basified by 3N NaOH solution and the precipitate was collected, washed with water and dried over vacuum oven to afford 1.7 g (95%) of the title compound as a gray solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.04 (dd, 1H), 8.56 (d, 1H), 8.47 (m, 2H), 8.41 (s, 1H), 7.92 (d, 1H), 7.75 (d, 1H), 7.64 (q, 1H). LCMS (method B): [MH]+=327, tR=2.03 min.

Workup

  1. additionwas added IBX (8.52 g, 45%, 13.69 mmol)
  2. temperatureat reflux for 1 day
  3. customThen the solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in 200 mL of water
  5. customthe precipitate was collected
  6. washwashed with water
  7. customdried over vacuum oven

Sources & evidence

ORD record
ord-9ae754eb6eff4d60adfa0a21f4a96998
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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