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

HRID 1892300Notes

Reaction equation

HRID 1892300 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%

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 affrode 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-fd711083ba844007a5cc9d47dcf65385
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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