4-(Tri-n-butylstannyl)pyridine → HCID 18182357, compound

HRID 1359297Notes

Reaction equation

HRID 1359297 reaction equation
FC(F)(F)S(O[C:7]1[N:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([Br:20])=[CH:9][CH:8]=1)(=O)=O.[N:23]1[CH:28]=[CH:27][C:26]([Sn](CCCC)(CCCC)CCCC)=[CH:25][CH:24]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.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.C1(C)C(C)=CC=CC=1>[CH2:13]([C:11]1[C:10]([Br:20])=[CH:9][CH:8]=[C:7]([C:26]2[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=2)[N:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 18182335HCID 18182335, compound

Product 1

HCID 18182357HCID 18182357, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 298 mg of 2-benzyl-3-bromo-6-pyridyl trifluoromethanesulfonate, 277 mg of (4-pyridyl)tributyltin, 87 mg of tetrakis(triphenylphosphine)palladium(0), 209 mg of tetrabutylammonium chloride and 5.0 ml of xylene was heated under stirring in an oil bath kept at 140° C. for one hour in a nitrogen atmosphere. After cooling as it was, the solvent was removed, and the residue was subjected to NH-silica gel column chromatography and eluted with hexane/ethyl acetate (5:1) and then with hexane/ethyl acetate (3:1), to give 196 mg of the target compound.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling as it
  3. customthe solvent was removed
  4. washeluted with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-e9e691fbe9474d1a8954c2beecfd099f
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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