2-(Tributylstannyl)pyrazine → (5-Pyrazin-2-yl-benzofuran-2-yl)-methanol

HRID 1070389Notes

Reaction equation

HRID 1070389 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[CH:7][C:6]=2[CH:12]=1.C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[N:22][CH:21]=[CH:20][N:19]=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>[N:19]1[CH:20]=[CH:21][N:22]=[CH:23][C:18]=1[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[CH:7][C:6]=2[CH:12]=1

Participants

5

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 2795537(5-Bromo-1-benzofuran-2-yl)methanol

Product 1

HCID 22396303(5-Pyrazin-2-yl-benzofuran-2-yl)-methanol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of (5-bromo-benzofuran-2-yl)-methanol (1 g, 4.4 mmol) and 2-tributylstannylpyrazine (1.6 g, 3.7 mmol) in 15 mL toluene at room temperature under argon, was added tetrakis(triphenylphosphine)palladium (0) (130 mg), and the mixture was heated at 95° C. overnight. The precipitate was allowed to cooled, extracted with ethyl acetate, washed with brine and dried over MgSO4. Filtration afforded 2.1 g of crude product that was further purified by chromatography to afford (5-pyrazin-2-yl-benzofuran-2-yl)-methanol.

Workup

  1. temperatureto cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. customafforded 2.1 g of crude product that
  7. customwas further purified by chromatography

Sources & evidence

ORD record
ord-8837625675bf4aea9a2323603cb16c19
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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