2-(Tributylstannyl)pyridine → HCID 68663288, compound

HRID 452725Notes

Reaction equation

HRID 452725 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)CCC>O1CCCC1.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>[CH3:16][C:13]1[O:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]3[O:4][CH:3]=[C:2]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[C:6]=3[CH:7]=2)=[N:15][N:14]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 44480697HCID 44480697, compound

Product 1

HCID 68663288HCID 68663288, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole (279 mg, 1.00 mmol), 2-(tri-n-butylstannyl)pyridine (0.384 mL, 1.20 mmol) and tetrakis(triphenylphosphine)palladium(0) (34.7 mg, 0.0300 mmol) in tetrahydrofuran (5 mL) was heated under reflux under an argon atmosphere for 85 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (hexane/tetrahydrofuran=1/1) and recrystallized from hexane/tetrahydrofuran to give the title compound (113 mg, yield 41%) as colorless crystals.

Workup

  1. temperatureunder reflux under an argon atmosphere for 85 hr
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by basic silica gel column chromatography (hexane/tetrahydrofuran=1/1)
  5. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-9f9411c3b924451cb3b0e0cbc3df11d1
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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