2-Pyridineacetic acid, hydrochloride (1:1) → 2-Pyridin-2-yl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone

HRID 269481

반응식

HRID 269481 반응식
CO[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].Cl.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21]C(O)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 2733832Lithium HexamethyldisilazideHCID 21110084methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate

생성물 1

HCID 598322452-Pyridin-2-yl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (200 mg, 1.13 mmol) and 2-pyridinyl-acetic acid hydrochloride (440 mg, 2.53 mmol) in anhydrous THF (10 mL) was added LiHMDS (1.0 M in THF, 10 mL, 10.0 mmol) at −78° C. The solution was stirred at −78° C. for 30 min and was allowed to warm up to RT. After stirring at RT for another 30 min, the reaction mixture was heated under reflux for 14 h. The solvent was then evaporated, the residue was taken up to ethyl acetate (50 mL), and washed with aq. NaHCO3. The organic layer was dried over MgSO4, filtered, and evaporated. The residue was used directly for the next reaction.

후처리

  1. temperatureto warm up to RT
  2. stirringAfter stirring at RT for another 30 min
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 14 h
  5. customThe solvent was then evaporated
  6. washwashed with aq. NaHCO3
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was used directly for the next reaction

출처 및 근거

ORD 기록
ord-ebe10ceb71664519a80050fdc239dbbd
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446199B2

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