Sodium Carbonate → HCID 18005129, compound

HRID 989193Notes

Reaction equation

HRID 989193 reaction equation
I[C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[N+:11]([C:4]1[CH:3]=[C:2]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 18005124HCID 18005124, compound

Product 1

HCID 18005129HCID 18005129, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2,3-Dihydro-7-iodo-5-nitrobenzofuran (0.76 g, 0.0026 mole) and 3-pyridylboronic acid (0.32 g, 0.0026 mole) in 50% aqueous 1,2-dimethoxyethane (50 ml) were treated under argon with sodium carbonate (1.17 g, 0.011 mole) and tetrakis triphenylphosphine palladium (0) (0.06 g, 0.000052 mole) and heated under reflux for 18 hours. The mixture was allowed to cool to ambient temperature, diluted with deionised water, extracted into ethyl acetate, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 30% ethyl acetate/60-80° petroleum ether to afford the title compound (0.19 g, 30%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. extractionextracted into ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with 30% ethyl acetate/60-80° petroleum ether

Sources & evidence

ORD record
ord-b66d7f24e9564c82873d4bff9d3a6d14
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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