Tetramethyltin → 4-Methoxy-3-methyl-6-[3-(trifluoromethyl)phenyl]pyridazine

HRID 52780Notes

Reaction equation

HRID 52780 reaction equation
Br[C:2]1[N:3]=[N:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:6][C:7]=1[O:8][CH3:9].[CH3:20][Sn](C)(C)C>CN(C=O)C.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[CH3:9][O:8][C:7]1[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=[N:3][C:2]=1[CH3:20]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 199596693-Bromo-4-methoxy-6-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 199596804-Methoxy-3-methyl-6-[3-(trifluoromethyl)phenyl]pyridazineYield 63%

Reagents, catalysts & solvents 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)CatalystHCID 6228DimethylformamideSolvent

Procedure

3-Bromo-4-methoxy-6-[3-(trifluoromethyl)phenyl]pyridazine (1.0 g, 0.003 mole, Compound No. 65), tetramethyltin (1.28 g, 0.0072 mole) and trans-benzyl(chloro)bis-(triphenylphosphine)palladium(II) (20 mg) were heated to 100° C. in DMF under N2 for 18 h. The reaction was then cooled and partitioned between aqueous KF solution and ethyl acetate. The KF solution was extracted with additional ethyl acetate. The organic layers were washed with brine, dried (MgSO4), filtered through silica gel and then evaporated in vacuo. The crude oil was then chromatographed on a Prep-500 to give 4-methoxy-3-methyl-6-[3-(trifluoromethyl)phenyl]pyridazine (0.51 g, 63% yield, Compound No. 66) as a light yellow solid.

Workup

  1. temperatureThe reaction was then cooled
  2. custompartitioned between aqueous KF solution and ethyl acetate
  3. extractionThe KF solution was extracted with additional ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through silica gel
  7. customevaporated in vacuo
  8. customThe crude oil was then chromatographed on a Prep-500

Sources & evidence

ORD record
ord-2ab40c400534466385ccf8fc97961d12
Source dataset
uspto-grants-1997_04
Patent number
US05616789

Reaction notes

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