2,6-Lutidine → HCID 19436809, compound

HRID 1735004Notes

Reaction equation

HRID 1735004 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[CH:5][C:4]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])=[N:3]1.Cl[C:16]1[N:17]=[N:18][CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.N1C(C)=CC=CC=1C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:23][O:22][C:20]1[CH:21]=[C:16]([O:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:8]([F:13])([F:14])[C:9]([F:11])([F:10])[F:12])[CH:5]=2)[N:17]=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 8857Ethyl AcetateHCID 109756123-Chloro-5-methoxypyridazineHCID 178481858HCID 178481858, compound

Product 1

HCID 19436809HCID 19436809, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Methyl-3-(pentafluoroethyl)-1H-pyrazol-5-ol (0.44 g, 0.002 mole), 3-chloro-5-methoxypyridazine (0.29 g, 0.002 mole), and 2,6-lutidine (0.27 g, 0.0024 mole) were refluxed under N2 in toluene (8 mL) for 15 h. This mixture was poured into ethyl acetate and washed with 7% HCl, water and then with saturated sodium bicarbonate. The organic layer was dried (MgSO4), filtered through silica gel with ethyl acetate, and evaporated in vacuo to give 5-methoxy-3-[[1-methyl-3-(pentafluoroethyl)-1H-pyrazol-5-yl]oxy]pyridazine as a light yellow solid. The compound was recrystallized to give (0.45 g, 69% yield) Compound 18, a white solid.

Workup

  1. washwashed with 7% HCl, water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered through silica gel with ethyl acetate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a16259c0ac4643e399bf3b455fc4feeb
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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