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

HRID 52777노트

반응식

HRID 52777 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c4f5200d2d045eca31be5cd692e2aba
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616789

반응 노트

불러오는 중…