Triacetoxyperiodinane → (6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3h-benzoimidazol-5-yl)-methanone

HRID 69232Notes

Reaction equation

HRID 69232 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:22]=[CH:21][C:16]4[N:17]=[CH:18][N:19]([CH3:20])[C:15]=4[CH:14]=3)[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[CH:22]=[CH:21][C:16]4[N:17]=[CH:18][N:19]([CH3:20])[C:15]=4[CH:14]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 87524278(Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3h-benzoimidazol-5-yl)-methanol

Product 1

HCID 87524396(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3h-benzoimidazol-5-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(3-methyl-3H-benzoimidazol-5-yl)-methanol (Stage 185.5, 1.03 g, 3.22 mmol) was suspended in DCM (30 mL). Dess-Martin periodinane (1.688 g, 3.86 mmol) was added and the mixture was stirred at rt for 1.5 h. The mixture was evaporated to dryness and the residue was taken in 1 M NaOH and sonicated. After 15 min of stirring, it was filtered. The precipitate was dried under vacuum overnight to afford the title compound (tR 2.18 min (conditions 8), MH+=312)

Workup

  1. customThe mixture was evaporated to dryness
  2. customsonicated
  3. stirringAfter 15 min of stirring
  4. filtrationit was filtered
  5. customThe precipitate was dried under vacuum overnight

Sources & evidence

ORD record
ord-da5304c9787049479e577e8f2499ba6f
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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