(3-Chloro-2-fluorophenyl)hydrazine → 4-(6-chloro-3-ethyl-7-fluoro-1H-indol-2-yl)-2-hydroxy-benzoic acid methyl ester

HRID 1160795노트

반응식

HRID 1160795 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH2:12][CH3:13])=[CH:6][C:5]=1[OH:15].[Cl:17][C:18]1[C:19]([F:26])=[C:20]([NH:24]N)[CH:21]=[CH:22][CH:23]=1>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:24][C:20]3[C:21]([C:11]=2[CH2:12][CH3:13])=[CH:22][CH:23]=[C:18]([Cl:17])[C:19]=3[F:26])=[CH:6][C:5]=1[OH:15]

참가 물질

5

반응물 2

HCID 2778381(3-Chloro-2-fluorophenyl)hydrazineHCID 595180214-Butyryl-2-hydroxy-benzoic acid methyl ester

생성물 1

HCID 595180204-(6-chloro-3-ethyl-7-fluoro-1H-indol-2-yl)-2-hydroxy-benzoic acid methyl ester

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 176Acetic Acid용매

반응 조건

온도
120 °C

실험 절차

A mixture of 4-butyryl-2-hydroxy-benzoic acid methyl ester (60 mg, 0.27 mmol), (3-chloro-2-fluoro-phenyl)-hydrazine (Apollo Scientific, Ltd., 54 mg, 0.27 mmol), and zinc chloride (110 mg, 0.8 mmol) in acetic acid (2 mL) is purged with nitrogen for 5 minutes and then heated in a sealed tube at 120° C. for 2 hours. The mixture is cooled to room temperature and diluted with ethyl acetate. The resulting mixture is sequentially washed with saturated aqueous Na2CO3 and saturated aqueous NaCl, and finally dried over sodium sulfate. After concentration, the crude product is purified via silica gel flash column chromatography (10% ethyl acetate in hexanes) to afford 4-(6-chloro-3-ethyl-7-fluoro-1H-indol-2-yl)-2-hydroxy-benzoic acid methyl ester as a light yellow solid: ESMS m/z 348.1 (M+H+).

후처리

  1. customis purged with nitrogen for 5 minutes
  2. temperatureThe mixture is cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washThe resulting mixture is sequentially washed with saturated aqueous Na2CO3 and saturated aqueous NaCl
  5. dry with materialfinally dried over sodium sulfate
  6. concentrationAfter concentration
  7. customthe crude product is purified via silica gel flash column chromatography (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-c96e38f34770433eaef37cda5194a561
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816542B2

반응 노트

불러오는 중…