Water → HCID 66680081, compound

HRID 1626730Notes

Reaction equation

HRID 1626730 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]([C:17]([NH:19][C:20]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].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.CO.C1(C)C=CC=CC=1>[Cl:30][C:27]1[CH:28]=[CH:29][C:20]([NH:19][C:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH:12]=2)=[O:18])=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 60794708HCID 60794708, compound

Product 1

HCID 66680081HCID 66680081, compoundYield 32.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

0.67 g (5.4 mmol) of 4-pyridine boronic acid, 1.0 g (2.7 mmol) of methyl 2-{[(3-bromophenyl)carbonyl]amino}-5-chlorobenzoate, 313 mg (0.27 mmol) of tetrakis(triphenylphosphine)palladium(0), and 0.58 g (5.4 mmol) of sodium carbonate were heated under reflux in a mixed solvent of 4 mL of water, 23 mL of toluene, and 6.7 mL of methanol for 7.5 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure. Ethyl acetate was added, and solids were collected by filtration. Subsequently, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 320 mg of methyl 5-chloro-2-({[3-(pyridin-4-yl)phenyl]carbonyl}amino)benzoate (yield: 32%).

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionEthyl acetate was added
  4. filtrationsolids were collected by filtration
  5. washSubsequently, the organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was then distilled off under reduced pressure
  8. customThe obtained crude product
  9. customwas separated
  10. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8492a4ee88b4a76bf9f490a63bbc4a3
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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