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

HRID 269481

反応式

HRID 269481 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ebe10ceb71664519a80050fdc239dbbd
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

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