Anthranilic Acid → 2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoic acid

HRID 969677Notes

Reaction equation

HRID 969677 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[NH:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH:20]=O)=[CH:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[NH:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH2:20][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[CH:12]1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 664154252-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of anthranilic acid (1.37 g, 1.0 mmol), 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1.46 g, 1.0 mmol), and p-toluenesulfonic acid mohohydrate (0.025 g, 0.13 mmol) in 30 mL of anhydrous toluene was stirred at reflux for 1 h. After being cooled to RT, NaBH4 (0.9 g) was added, and the mixture was stirred at RT for 30 min. The reaction was quenched with MeOH, and the volatiles were removed under reduced pressure. The residue was taken up in water, AcOH was added to bring pH to 4, and the mixture was extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, and condensed. The residue was purified by flash column chromatography to give the titled compound. MS (ES+): 268.1 (M+H)+. Calc'd for C15H13N3O2-267.10.

Workup

  1. temperatureat reflux for 1 h
  2. stirringthe mixture was stirred at RT for 30 min
  3. customThe reaction was quenched with MeOH
  4. customthe volatiles were removed under reduced pressure
  5. additionAcOH was added
  6. extractionthe mixture was extracted with EtOAc
  7. washThe combined organic portions were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customcondensed
  11. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-55702dab23e34f6fb3ccd5bb45c9a4e9
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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