Sodium Carbonate → Ethyl 3-[4-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate

HRID 628835Notes

Reaction equation

HRID 628835 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=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+]>C(#N)C.O.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>[CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[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:7]=2)=[CH:9][CH:10]=1)([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3249312(3-Ethoxycarbonylphenyl)boronic acidHCID 837125462-Chloro-4-(4-isopropyl-phenyl)-pyridine

Product 1

HCID 69232425Ethyl 3-[4-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoateYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Part D. A solution of 2-chloro-4-(4-isopropyl-phenyl)-pyridine (110 mg, 0.48 mmol) in acetonitrile-water (1 mL/0.5 mL) is treated with 3-carboethoxybenzeneboronic acid (186 mg, 0.96 mmol), sodium carbonate (153 mg, 1.44 mmol) and tetrakis(triphenylphosphine)palladium (cat. amount). The mixture is heated to reflux for 12 h., then cooled and partitioned between water and ethyl acetate. The organic phase is washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue is separated by column chromatography to afford ethyl 3-[4-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate (116 mg, 70%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 12 h.
  3. temperaturecooled
  4. custompartitioned between water and ethyl acetate
  5. washThe organic phase is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is separated by column chromatography

Sources & evidence

ORD record
ord-e11ee903789a42608c55a2684d397fb0
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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