3-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine → 3-Chloro-6-(4-fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine

HRID 633513Notes

Reaction equation

HRID 633513 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH2:9][CH2:10][C:5]2=[N:4][N:3]=1

Participants

4

Reactant 1

HCID 446043783-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 675246973-Chloro-6-(4-fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazineYield 87%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

790 mg of zinc powder are added to a mixture of 300 mg of 3-chloro-6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazine in 10 cm3 of glacial acetic acid at 20° C. After stirring for 1 h, the suspension is filtered and the filtrate is concentrated to dryness under vacuum. The oily residue is purified by dry deposit on Biotage Quad 12M (KP-SIL, 60 A; 32-63 μm), elution being carried out with a 95:5 mixture of dichloromethane/methanol. 263 mg of 3-chloro-6-(4-fluorophenyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine are thus obtained in the form of a yellowy-brown powder, the characteristics of which are as follows:

Workup

  1. filtrationthe suspension is filtered
  2. concentrationthe filtrate is concentrated to dryness under vacuum
  3. customThe oily residue is purified
  4. customby dry deposit on Biotage Quad 12M (KP-SIL, 60 A
  5. wash32-63 μm), elution
  6. additionbeing carried out with a 95:5 mixture of dichloromethane/methanol

Sources & evidence

ORD record
ord-5719a8c48dae4bfc886e486be2db43eb
Source dataset
uspto-grants-2016_04
Patent number
US09321777B2

Reaction notes

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