Toluene → HCID 67380727, compound

HRID 1422841Notes

Reaction equation

HRID 1422841 reaction equation
C1(C)C=CC=CC=1.[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1.CC(C)([O-])C.[Na+].Cl[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)[CH:12]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 276852,5-DichloropyridineHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 23676156Sodium t-butoxide

Product 1

HCID 67380727HCID 67380727, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 962WaterSolvent

Procedure

To a toluene (10.0 mL) solution of 3-amino-benzoic acid methyl ester (330 mg, 2.2 mmol) was added palladium acetate (200 μL of 0.001 mmol stock solution), BINAP (200 μL of 0.001 mmol stock colution), sodium t-butoxide (2.2 mmol) and 2,5-dichloro-pyridine (296 mg, 2.0 mmol). The reaction mixture was refluxed for 10 h. Collected crude reaction mass was added to water, extracted with ethyl acetate. Solvent was evaporated and the crude mass was purified by flash column chromatography using 20% ethyl acetate in hexanes on a prepacked silica column to give 3-(5-chloro-pyridin-2-ylamino)-benzoic acid methyl ester (315 mg).

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. customCollected crude
  3. customreaction mass
  4. extractionextracted with ethyl acetate
  5. customSolvent was evaporated
  6. customthe crude mass was purified by flash column chromatography

Sources & evidence

ORD record
ord-f4612f1401b544df8235218321d66fae
Source dataset
uspto-grants-2015_01
Patent number
US08927549B2

Reaction notes

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