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

HRID 1634098Notes

Reaction equation

HRID 1634098 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e20b395a26b34907861e7eb25b0bbb3a
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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