Ethyl Acetate → HCID 19436801, compound

HRID 1735018Notes

Reaction equation

HRID 1735018 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:5]=[N:6][CH:7]=1.[CH2:19](C([Sn])=C(CCCC)CCCC)[CH2:20]CC.C(OCC)(=O)C>CN(C=O)C>[CH:19]([C:2]1[CH:3]=[C:4]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:5]=[N:6][CH:7]=1)=[CH2:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 19436792HCID 19436792, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 19436801HCID 19436801, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy]pyridazine (2.0 g, 0.0066 mole), tributylvinyltin (2.3 g, 0.00726 mole) and Pd(PhCH2)Cl(Ph3P)2 (0.1 g, 0.000132 mole) were heated at 100° C. in DMF (75 mL) for 1 hour. The mixture was then poured into ethyl acetate and extracted 2×200 mL with aqueous KF, brine, dried (MgSO4), filtered through a pad of silica gel with ethyl acetate and evaporated in vacuo. The crude oil was purified by silica gel chromatography to give 5-ethenyl-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy]pyridazine (1.62 g, 91% yield) as an off-white solid.

Workup

  1. extractionextracted 2×200 mL with aqueous KF, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered through a pad of silica gel with ethyl acetate
  4. customevaporated in vacuo
  5. customThe crude oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3dd0bd3c5bc1456ab4980e8c4ce5560f
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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