O-Xylene → 4-Benzyl-5-bromo-2-(3,4-methylenedioxyphenyl)pyridine

HRID 1359289Notes

Reaction equation

HRID 1359289 reaction equation
FC(F)(F)S(O[C:7]1[CH: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][N:8]=1)(=O)=O.[CH2:23]1[O:31][C:30]2[CH:29]=[CH:28][C:27]([Sn](CCCC)(CCCC)CCCC)=[CH:26][C:25]=2[O:24]1.C1(C)C(C)=CC=CC=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>[CH2:13]([C:11]1[C:10]([Br:20])=[CH:9][N:8]=[C:7]([C:28]2[CH:27]=[CH:26][C:25]3[O:24][CH2:23][O:31][C:30]=3[CH:29]=2)[CH:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 11112375Stannane, 1,3-benzodioxol-5-yltributyl-HCID 181821814-Benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate

Product 1

HCID 181822494-Benzyl-5-bromo-2-(3,4-methylenedioxyphenyl)pyridineYield 38.1%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 400 mg of 4-benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate, 410 mg of (3,4-methylenedioxyphenyl)tributyltin, 300 mg of tetrabutylammonium chloride, 20 mg of tetrakis(triphenylphsphine)palladium(0) and 2 ml of xylene was stirred under heating for 3 hours in an oil bath kept at 140° C. in a nitrogen atmosphere. The reaction solution was subjected to silica gel column chromatography using 5-10% ethyl acetate/hexane, to give 140 mg of the title compound.

Workup

  1. temperatureunder heating for 3 hours in an oil bath
  2. customkept at 140° C. in a nitrogen atmosphere

Sources & evidence

ORD record
ord-b049a19658c6490ab28dc1781d34c672
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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