2-(Tributylstannyl)pyridine → 2-(4-Bromothiophen-2-yl)pyridine

HRID 2109447Notes

Reaction equation

HRID 2109447 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[CH:6]=1.C([Sn](CCCC)(CCCC)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)CCC>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>[Br:7][C:5]1[CH:6]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[S:3][CH:4]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 2724560Thiophene, 2,4-dibromo-

Product 1

HCID 142923562-(4-Bromothiophen-2-yl)pyridineYield 73.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2,4-Dibromothiophene (695 mg, 2.87 mmol), 2-(tri-n-butylstannyl)pyridine (830 mg, 1.92 mmol), and tetrakis(triphenylphosphine)palladium (0) (220 mg, 0.19 mmol) were refluxed in 3 mL of toluene at 120° C. overnight. After filtrated out of solid residue, the reaction mixture was purified by flash chromatography using a gradient of ethyl acetate in hexane to give a beige solid as the title compound (340 mg), m/z 240, 242 (MH+).

Workup

  1. filtrationAfter filtrated out of solid residue
  2. customthe reaction mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-05b3081110b94922bd653edd2e0ac883
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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