4-Nitrophenol → 4-(4-Nitrophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester

HRID 387969노트

반응식

HRID 387969 반응식
CN1CCCC1=O.C(N(C(C)C)CC)(C)C.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:19])=[O:18].[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38](Cl)=[C:33]2[CH:32]=1)=[O:30]>O>[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38]([O:26][C:23]3[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=3)=[C:33]2[CH:32]=1)=[O:30]

참가 물질

6

반응물 4

HCID 9804-NitrophenolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 589308884-Chloro-furo[2,3-b]pyridine-2-carboxylic acid methyl ester

생성물 1

HCID 589314974-(4-Nitrophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester수율 4.7%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

After adding N-methylpyrrolidone (4.0 ml), diisopropylethylamine (1.3 ml) and para-nitrophenol (822 mg) to 4-chlorofuro[2,3-b]pyridine-2-carboxylic acid methyl ester (1.0 g), the mixture was heated and stirred at 140° C. for 5 hours. After cooling, water was added, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Tetrahydrofuran was used for recrystallization to obtain the title compound (70 mg).

후처리

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. extractionextraction
  4. washthe organic layer was washed with water and saturated saline in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customTetrahydrofuran was used for recrystallization

출처 및 근거

ORD 기록
ord-e932449599b64eeea7beccf39108804f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372981B2

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