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

HRID 456080Notes

Reaction equation

HRID 456080 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.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

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 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 2-iodoxybenzoic acid (8.52 g, 45%, 13.69 mmol) and the reaction mixture was stirred at reflux for 1 day. 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 (yield: 95%) 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. temperatureat reflux for 1 day
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in 200 mL of water
  4. customthe precipitate was collected
  5. washwashed with water
  6. customdried over vacuum oven

Sources & evidence

ORD record
ord-9e0c37dcc3be4fbfbab5994c0f686585
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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