Potassium Hydroxide → 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 1821805노트

반응식

HRID 1821805 반응식
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([O:13]CC)=[O:12])[NH:8][C:7]=12.[OH-].[K+]>O1CCCC1.CO>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[NH:8][C:7]=12

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 46839972ethyl 7-chloro-1H-pyrrolo(2,3-c)pyridine-2-carboxylate

생성물 1

HCID 768529167-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid수율 94.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.64 g, 2.85 mmol) was dissolved in tetrahydrofuran (5.7 mL) and methanol (6.8 mL). To the mixture was added 3 N KOH (2.85 mL). After stirring overnight (15.5 h) at room temperature, the reaction mixture was concentrated to dryness. The residue was dissolved in water. This aqueous solution was made acidic (pH 3) using 6 N HCl. The precipitate was collected by filtration. The precipitate was dissolved in methanol and concentrated to dryness to afford 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (0.53 g, 2.7=mmol, 94%) as a yellow powder: mp 210-214° C.; 1H NMR (300 MHz, CD3OD) δ7.25 (1H, s), 7.65 (1H, d, J=5.4 Hz), 7.94 (1H, d, J=5.4 Hz); ESI MS m/z 195 [C8H5ClN2O2—H]−; HPLC (Method A) >99% (AUC), tR=12.2 min.

후처리

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in water
  3. filtrationThe precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in methanol
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-d296640081d842e2a1fed356f4210d6b
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

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