2-Fluoro-4-nitrophenol → 7-(2-Fluoro-4-nitrophenoxy)-2-(1-isopropyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine

HRID 418639노트

반응식

HRID 418639 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH:16]([CH3:18])[CH3:17])[CH:15]=3)[S:10][C:3]=12.[F:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[OH:29].C(=O)([O-])[O-].[K+].[K+].CO.C(Cl)Cl>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[O:29][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH:16]([CH3:18])[CH3:17])[CH:15]=3)[S:10][C:3]=12

참가 물질

6

반응물 4

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 587903417-Chloro-2-(1-isopropyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine

생성물 1

HCID 587903897-(2-Fluoro-4-nitrophenoxy)-2-(1-isopropyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine수율 88.3%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

반응 조건

온도
195 °C

실험 절차

To a solution of 123 (1.16 g, 4.18 mmol) in Ph2O (20 ml) was added 2-fluoro-4-nitrophenol (1.31 g, 8.37 mmol) and potassium carbonate (2.31 g, 16.72 mmol). The reaction mixture was heated to 195° C. for 18 hrs then cooled to room temperature. The residue was purified by column chromatography, eluents EtOAc/Hex (9/1 to 5/5), then MeOH/CH2Cl2 (98/2), to afford title compound 124 (1.47 g, 88% yield) as a yellow solid. MS (m/z): 399.0 (M+H).

후처리

  1. temperaturethen cooled to room temperature
  2. customThe residue was purified by column chromatography, eluents EtOAc/Hex (9/1 to 5/5)

출처 및 근거

ORD 기록
ord-098e42ea24f942b5a4958cae0bf3c052
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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