Water → HCID 69234837, compound

HRID 628841Notes

Reaction equation

HRID 628841 reaction equation
Cl[C:2]1[CH: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][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:25]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)([CH3:27])[CH3:26].O>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:25]([C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH: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][N:3]=2)=[CH:30][CH:29]=1)([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27734804-Isopropylphenylboronic acidHCID 86620267HCID 86620267, compound

Product 1

HCID 69234837HCID 69234837, compoundYield 76%

Reagents, catalysts & solvents 2

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

Procedure

Part C. A solution of ethyl 3-(2-chloro-pyridin-4-yl)-benzoate (81 mg, 0.31 mmol), sodium carbonate (99 mg, 0.93 mmol) and 4-isopropylbenzeneboronic acid (60 mg) in acetonitrile-water (2 mL/0.5 mL) is treated with a catalytic quantity of tetrakis(triphenylphosphine)palladium, and heated to reflux for 24 h. The mixture is poured into water (60 mL), and this mixture is extracted with diethyl ether (3×60 mL). The extracts are combined, washed with brine, dried over magnesium sulfate, filtered and evaporated to afford ethyl 3-[2-(4-isopropyl-phenyl)-pyridin-4-yl]-benzoate (75 mg, 76%)

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. extractionthis mixture is extracted with diethyl ether (3×60 mL)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-99449814ec2d454d80ad5c361cb12746
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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