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

HRID 456046Notes

Reaction equation

HRID 456046 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 then 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 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-62cc9408a3114ab9a8048bd5cae8609b
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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