(6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanol → 6-Chloroimidazo[1,2-b]pyridazine-3-carbaldehyde

HRID 1959637Notes

Reaction equation

HRID 1959637 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][OH:12])=[CH:9][N:10]=2)[N:7]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)[N:7]=1

Participants

4

Reactant 1

HCID 57352521(6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanol

Product 1

HCID 114467026-Chloroimidazo[1,2-b]pyridazine-3-carbaldehydeYield 54.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-methanol (1.3 g, 7.1 mmol) in DCM (50 mL) was added active MnO2 (3 g, 34.5 mmol). The mixture was stirred at rt overnight and filtered. The filtrate was concentrated under vacuum and the residue was washed with EtOAc to afford 6-chloro-imidazo[1,2-b]pyridazine-3-carbaldehyde (0.7 g) in 54% yield. 1H-NMR (400 MHz, CDCl3) δ ppm 10.36 (s, 1H), 8.42 (s, 1H), 8.08 (d, 1H), 7.38 (d, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum
  3. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-321f4162416247a99731eee8cde3ba02
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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