Tributylvinyltin → 1(4'-Nitrophenyl)-5-ethenyl-3-methylpyrazole

HRID 1634098노트

반응식

HRID 1634098 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](Br)=[CH:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:17]([Sn](CCCC)(CCCC)CCCC)=[CH2:18]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH:17]=[CH2:18])=[CH:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 81998TributylvinyltinHCID 114829301-(4'-Nitrophenyl)-5-bromo-3-methylpyrazole

생성물 1

HCID 154391171(4'-Nitrophenyl)-5-ethenyl-3-methylpyrazole수율 92%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(4′-nitrophenyl)-5-bromo-3-methylpyrazole (138 mg, 0.49 mmol) in THF (5 mL) was added Pd(PPh3)4 (21 mg, 0.018 mmol) followed by vinyl tributyltin (0.16 mL, 0.54 mmol). The mixture was heated at reflux for 6 hr under N2, and was then quenched with saturated KF and extracted with EtOAc. The extract was dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel (hexane/acetate, 10:1) to give the title compound (103 mg, 92%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hr under N2
  3. customwas then quenched with saturated KF
  4. extractionextracted with EtOAc
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane/acetate, 10:1)

출처 및 근거

ORD 기록
ord-e20b395a26b34907861e7eb25b0bbb3a
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506747B1

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