Sodium Carbonate → HCID 69234812, compound

HRID 628838Notes

Reaction equation

HRID 628838 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.[C:17]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>>[CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:7]=[C:2]([C:26]3[CH:27]=[C:22]([CH:23]=[CH:24][CH:25]=3)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:3]=[N:4][CH:5]=2)=[CH:9][CH:10]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 3249312(3-Ethoxycarbonylphenyl)boronic acidHCID 69234639HCID 69234639, compound

Product 1

HCID 69234812HCID 69234812, compoundYield 79%

Conditions

Temperature
80 °C

Procedure

Part B. A solution of 3-bromo-5-(4-isopropyl-phenyl)-pyridine (300 mg, 1.1 mmol) and 3-carboethoxybenzeneboronic acid (180 mg, 1.1 mmol) in ethanol-toluene-water (10 mL/5 mL/3 mL) is treated with sodium carbonate (345 mg), degassed twice and treated with a catalytic quantity of tetrakis(triphenylphosphine)palladium. The mixture is heated to 80° C. with stirring until the starting material is consumed as determined by TLC. Then, 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, and the residue is separated by column chromatography to afford ethyl 3-[5-(4-isopropyl-phenyl)-pyridin-3-yl]-benzoate (252 mg, 79%).

Workup

  1. customdegassed twice
  2. additiontreated with a catalytic quantity of tetrakis(triphenylphosphine)palladium
  3. customis consumed
  4. temperatureThen, the mixture is cooled
  5. filtrationfiltered
  6. customevaporated
  7. customthe residual material is partitioned between water and ethyl acetate
  8. washThe organic phase is washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customthe residue is separated by column chromatography

Sources & evidence

ORD record
ord-3b2ce5461f1d4b76904d69829d2513f0
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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