Triacetoxyperiodinane → (6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(5,7-difluoro-quinolin-6-yl)-methanone

HRID 69226Notes

Reaction equation

HRID 69226 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[C:14]([F:24])=[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(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[C:14]([F:24])=[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 159087TriacetoxyperiodinaneHCID 58147519(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

Product 1

HCID 87523812(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(5,7-difluoro-quinolin-6-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(5,7-difluoro-quinolin-6-yl)-methanol (Stage 182.4, 3.0 g, 8.65 mmol) was dissolved in DCM (87 mL) and Dess-Martin periodinane (4.40 g, 10.38 mmol) was added. The RM was stirred for 3 h at rt. The solvent was removed and the residue was then taken up with EtOAc and washed with 2.5 M NaOH and with brine. The organic layer was then dried over Na2SO4 and the solvent was removed to give the title compound as a brown solid (tR 1.2 min (conditions 2), MH+=345).

Workup

  1. customThe solvent was removed
  2. washwashed with 2.5 M NaOH and with brine
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-fdc90ff625ae4f8ea3137d6d3d2f47d1
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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