Methanol → 3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine-7-carbaldehyde

HRID 1896464Notes

Reaction equation

HRID 1896464 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][N:5]2[C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=[C:4]2[CH:3]=1.C[OH:16]>ClCCl>[F:13][C:11]([F:14])([F:12])[C:8]1[N:5]2[N:6]=[CH:7][C:2]([CH:1]=[O:16])=[CH:3][C:4]2=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 536292037-Methyl-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 536292043-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine-7-carbaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A finely-ground powder of NaIO4 is added to a solution of 7-methyl-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine x233 (0.52 g, 2.0 mmol) in absolute methanol (42 ml). The reaction mixture is stirred at room temperature for 1.5 h and diluted with an equal volume of dichloromethane. The mixture is filtered through the Celite layer, and the solvents are removed under reduced pressure. The residue (0.5 g) is purified by chromatography on silicagel (hexane/ethyl acetate 3/2) to yield 0.34 g of 3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine-7-carbaldehyde x235 as a white solid.

Workup

  1. filtrationThe mixture is filtered through the Celite layer
  2. customthe solvents are removed under reduced pressure
  3. customThe residue (0.5 g) is purified by chromatography on silicagel (hexane/ethyl acetate 3/2)

Sources & evidence

ORD record
ord-e6c4ec8a6d0b43a2b685873404dfaf42
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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