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

HRID 2043687Notes

Reaction equation

HRID 2043687 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 NaI4 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-37a5fbae97884f46a2db07ed3ec2128b
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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