Sodium Carbonate → HCID 69234198, compound

HRID 628843Notes

Reaction equation

HRID 628843 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:4][CH:3]=1.[CH:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([CH3:21])[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=3)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27734804-Isopropylphenylboronic acidHCID 86620268HCID 86620268, compound

Product 1

HCID 69234198HCID 69234198, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Part B. A solution of ethyl 3-(6-bromo-pyridin-2-yl)-benzoate (154 mg, 0.5 mmol) and 4-isopropylbenzeneboronic acid (83 mg, 0.5 mmol) in acetonitrile is treated with a solution of sodium carbonate (160 mg) in water (1 mL). The mixture is degassed twice, and a catalytic amount of tetrakis(triphenylphosphine)palladium is added under the protection of nitrogen. The reaction mixture is stirred at 80° C. until the consumption of starting material is observed by TLC. The mixture is cooled, filtered and evaporated, and the residual material is partitioned between water and ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate, filtered and evaporated. The residue is purified by column chromatography to afford ethyl 3-[6-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate (120 mg, 69%).

Workup

  1. customThe mixture is degassed twice
  2. additiona catalytic amount of tetrakis(triphenylphosphine)palladium is added under the protection of nitrogen
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. customevaporated
  6. customthe residual material is partitioned between water and ethyl acetate
  7. washThe organic phase is washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-f164996f15e04dd8a55bf0096c25554e
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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