Benzyl Alcohol → 3-Chloro-6-(4-[1,2,3]triazol-1-yl-butyl)-pyridazine

HRID 349238Notes

Reaction equation

HRID 349238 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]#[C:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)=[CH:6][CH:7]=1.C(O)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>C(OCC)(=O)C.[Pd].C1COCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 23676156Sodium t-butoxideHCID 860740673-Chloro-6-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridazine

Product 1

HCID 860740683-Chloro-6-(4-[1,2,3]triazol-1-yl-butyl)-pyridazine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3-Chloro-6-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridazine (2.50 g, 10.7 mmol) is dissolved in ethyl acetate (450 ml) and hydrogenated for 3.5 h at r.t. in the presence of palladium on charcoal (10%, 2.50 g). The reaction mixture is filtered and concentrated in vacuo. The residue was dissolved in THF (10 ml) and added to a solution of benzyl alcohol (0.94 ml, 9.0 mmol) and sodium tert-butoxide (NaOtBu) (0.842 g, 8.76 mmol) in THF (80 ml). After stirring for 2 h ethyl acetate (100 ml) is added, the mixture is washed with saturated ammonium chloride (NH4Cl), dried over Na2SO4 and concentrated in vacuo. After flash column chromatography (ethyl acetate) 3-chloro-6-(4-[1,2,3]triazol-1-yl-butyl)-pyridazine is obtained as a colorless solid. Yield 1.14 g (45%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in THF (10 ml)
  4. additionis added
  5. washthe mixture is washed with saturated ammonium chloride (NH4Cl)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86f6a98e2b98485aa44731fcba163928
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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