Tri(butyl)vinyltin → HCID 58958600, compound

HRID 915573Notes

Reaction equation

HRID 915573 reaction equation
Br[C:2]1[C:3]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[N:4][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[C:6]=1[NH2:7].[CH2:22](C([Sn])=C(CCCC)CCCC)[CH2:23]CC>C1(C)C=CC=CC=1.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>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:3]2[C:2]([CH:22]=[CH2:23])=[C:6]([NH2:7])[N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH3:14])[N:4]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 692765564-Bromo-3-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-amine

Product 1

HCID 58958600HCID 58958600, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-bromo-3-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-amine (200 mg, 0.58 mmol) in toluene (10 mL) was added tributylvinyl tin (0.33 mL, 366 mg, 1.16 mmol) and tetrakis(triphenylphosphine)palladium(0) (66 mg, 0.06 mmol). The reaction mixture was heated to reflux and stirred for 16 h. After cooling to rt, the mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (100 mL), washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Silica gel flash chromatography of the residue using 10% EtOAc/Hex afforded 3-(4-fluorophenyl)-1-(2-methylphenyl)-4-vinyl-1H-pyrazol-5-amine (87 mg, 51%):

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationthe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a47c35be9b24f8ba37b8f5cc3ce36b7
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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