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

HRID 54656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54656
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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f784d83324384c11a02788add6a08287
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623072

Notizen zur Reaktion

Wird geladen…