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

HRID 969677노트

반응식

HRID 969677 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-55702dab23e34f6fb3ccd5bb45c9a4e9
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307088B2

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