Sodium Carbonate → HCID 44251152, compound

HRID 1963998Notes

Reaction equation

HRID 1963998 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:35])[CH2:19][O:20][CH2:21][C:22]([NH:24][C:25]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=2[C:27]([OH:29])=[O:28])=[O:23])[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[Cl:34][C:31]1[CH:32]=[CH:33][C:25]([NH:24][C:22](=[O:23])[CH2:21][O:20][CH2:19][C:18](=[O:35])[NH:17][C:13]2[CH:12]=[CH:11][CH:16]=[C:15]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:14]=2)=[C:26]([CH:30]=1)[C:27]([OH:29])=[O:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 866533492-[((2-[(3-Bromophenyl)amino]-2-oxoethoxy)acetyl)amino]-5-chlorobenzoic acid

Product 1

HCID 44251152HCID 44251152, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

0.48 g (3.88 mmol) of 3-pyridineboronic acid, 1.3 g (2.85 mmol) of 2-[((2-[(3-bromophenyl)amino]-2-oxoethoxy)acetyl)amino]-5-chlorobenzoic acid.methyl ester, 95.9 mg (0.08 mmol) of tetrakis(triphenyl phosphine)palladium (0), and 0.41 g (3.88 mmol) of 2N sodium carbonate were heated under reflux for 8 hours in 9.2 mL of toluene and 2.6 mL of methanol. After completion of the reaction, the solvent was distilled off under reduced pressure, and ethyl acetate was added to separate the solid by filtration. Thereafter, the organic layer was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography to give 5-chloro-2-([(2-oxo-2-([3-(pyridin-3-yl)phenyl]amino)ethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 62%).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure, and ethyl acetate
  3. additionwas added
  4. customto separate the solid
  5. filtrationby filtration
  6. washThereafter, the organic layer was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe resulting crude product was separated
  10. custompurified

Sources & evidence

ORD record
ord-0574b322dfe94963bd0d7f9a75e9921f
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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