Tributylvinyltin → 4-Ethenyl-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine

HRID 52777ノート

反応式

HRID 52777 の反応式
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[N:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.[CH:20]([Sn](CCCC)(CCCC)CCCC)=[CH2:21]>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+]>[CH:20]([C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[N:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)=[CH2:21]

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 199596684-Bromo-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine

生成物 1

HCID 199596644-Ethenyl-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine収率 42%

試薬・触媒・溶媒 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)触媒HCID 6228Dimethylformamide溶媒

実験手順

4-Bromo-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine (1.0 g, 0.003 mole, Compound No. 57), vinyltributyltin (1.1 g, 0.0034 mole) and trans-benzyl(chloro)bis-(triphenylphosphine)-palladium(II) (20 mg) were heated to 110° C. in DMF (50 mL) under N2 for 4 h. The reaction was then cooled and partitioned between aqueous KF 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-ethenyl-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine (0.35 g, 42% yield, Compound No. 55) as a light brown solid.

後処理

  1. temperatureThe reaction was then cooled
  2. custompartitioned between aqueous KF 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

出典と根拠

ORDレコード
ord-3c4f5200d2d045eca31be5cd692e2aba
出典データセット
uspto-grants-1997_04
特許番号
US05616789

反応ノート

読み込み中…