Sodium Carbonate → HCID 86620268, compound

HRID 628842Notes

Reaction equation

HRID 628842 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)([O:11][CH2:12][CH3:13])=[O:10].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[Br:8][C:4]1[N:3]=[C:2]([C:18]2[CH:19]=[C:14]([CH:15]=[CH:16][CH:17]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 122742,6-DibromopyridineHCID 3249312(3-Ethoxycarbonylphenyl)boronic acid

Product 1

HCID 86620268HCID 86620268, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Part A. A solution of 2,6-dibromopyridine (6.16 g, 26 mmol) and 3-carboethoxybenzeneboronic acid (0.5 g, 2.6 mmol) in acetonitrile (20 mL) is treated with a solution of sodium carbonate (0.88 g) in water (5 mL). The mixture is degassed twice, and a catalytic amount of tetrakis(triphenylphosphine)palladium is added. The reaction mixture is heated to 80° C. and stirred for 12 h., then cooled, filtered and evaporated. The residue is partitioned between water and ethyl acetate, and the organic phase is washed with satd. aq. brine, dried over sodium sulfate, filtered and evaporated. The residual material is separated by column chromatography to give ethyl 3-(6-bromo-pyridin-2-yl)-benzoate (154 mg, 20%).

Workup

  1. customThe mixture is degassed twice
  2. additiona catalytic amount of tetrakis(triphenylphosphine)palladium is added
  3. temperaturecooled
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is partitioned between water and ethyl acetate
  7. washthe organic phase is washed with satd
  8. dry with materialaq. brine, dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residual material is separated by column chromatography

Sources & evidence

ORD record
ord-2b1e68c56a8d47b09cefcaa7fcdf6387
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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