Ethyl 4,4,4-trifluoroacetoacetate → 1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

HRID 402478

반응식

HRID 402478 반응식
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:3]1.C([O:16][C:17](=O)[CH2:18][C:19](=O)[C:20]([F:23])([F:22])[F:21])C>C(O)(=O)C>[CH3:1][N:2]1[C:6]2[NH:7][C:17](=[O:16])[CH:18]=[C:19]([C:20]([F:23])([F:22])[F:21])[C:5]=2[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:3]1

참가 물질

4

반응물 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 5177791-Methyl-3-phenyl-1H-pyrazol-5-amine

생성물 1

HCID 1363765221-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one수율 24.3%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
150 °C

실험 절차

A mixture of 1-methyl-3-phenyl-1H-pyrazol-5-amine (1.7 g, 9.815 mmol) and 4,4,4-Trifluoro-3-oxo-butyric acid ethyl ester (2.168 g, 11.776 mmol) in acetic acid (3.0 mL) was heated at 150° C. for 10 h in a sealed tube under constant stirring. The reaction mixture was cooled to rt and poured into rapidly stirred ice-cold water to obtain the crude product as a solid. The product was collected by filtration and dried under vacuum. The product was purified by flash-chromatography (eluent: 35% EtOAc in hexane) to yield the title compound as a white solid (0.7 g, 24%). [1H-NMR (CDCl3, 300 MHz) δ 13.65 (s, 1H), 7.52-7.37 (m, 5H), 6.78 (s, 1H), 4.20 (s, 3H); LCMS RtC=1.430 min; [M+H]+=294.0]

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. additionpoured into rapidly stirred ice-cold water
  3. customto obtain the crude product as a solid
  4. filtrationThe product was collected by filtration
  5. customdried under vacuum
  6. customThe product was purified by flash-chromatography (eluent: 35% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-9ac53d9a1cf64b9fbaff364aece16c93
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742106B2

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