Tri(butyl)vinyltin → HCID 58961287, compound

HRID 916626Notes

Reaction equation

HRID 916626 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][N:11]=1.[CH2:17](C([Sn])=C(CCCC)CCCC)[CH2:18]CC>C1(C)C=CC=CC=1.C(OCC)(=O)C.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:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:17]=[CH2:18])=[CH:12][N:11]=1

Participants

6

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 58961248HCID 58961248, compound

Product 1

HCID 58961287HCID 58961287, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (2,6-Difluoro-phenyl)-(5-iodo-pyridin-2-yl)-amine and Pd(PPh3)4 (approximately 10 mol %) in toluene (approximately. 80 mL/g) at room temperature was added tributylvinyltin (1.1 eq.). The reaction was placed under a N2 atmosphere and heated to 80° C. overnight. The solution was cooled, diluted with ethyl acetate (approximately 80 mL/g) and filtered through a pad of celite. The celite was washed with a further portion of ethyl acetate. The organic layer was dried over MgSO4 and concentrated in vacuo to give the crude reaction product as a yellow oil. Purification by column chromatography, using 10% ethyl acetate:hexane as eluant provided (2,6-Difluoro-phenyl)-(5-vinyl-pyridin-2-yl)-amine (Rf 0.14) in 66% yield.

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered through a pad of celite
  3. washThe celite was washed with a further portion of ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude
  7. customreaction product as a yellow oil
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-29a645802c1f43dcb1f7444268277350
Source dataset
uspto-grants-2007_09
Patent number
US07271181B2

Reaction notes

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