Hydrochloric Acid → Ethyl 5-(2-fluoro-4-methoxyphenyl)-6-methyl-1H-indazole-3-carboxylate

HRID 1054803노트

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HRID 1054803 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7](COCC[Si](C)(C)C)[N:8]=[C:9]2[C:14]=1[CH:13]=[C:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[F:23])[C:11]([CH3:24])=[CH:10]2)=[O:5])[CH3:2].Cl>CCO>[F:23][C:16]1[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[CH3:24])[NH:8][N:7]=[C:6]2[C:4]([O:3][CH2:1][CH3:2])=[O:5]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86698794Ethyl 5-(2-fluoro-4-methoxyphenyl)-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-3-carboxylate

생성물 1

HCID 86698795Ethyl 5-(2-fluoro-4-methoxyphenyl)-6-methyl-1H-indazole-3-carboxylate수율 93%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

To a solution of 5-(2-fluoro-4-methoxyphenyl)-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole-3-carboxylic acid ethyl ester (440 mg, 0.96 mmol) in EtOH (6 mL) was added 3 N HCl solution (1.5 mL, 4.5 mmol). The reaction mixture was heated to 90° C. for 1 hour, cooled to room temperature and concentrated in vacuo. The residue was partitioned between water and EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound (292 mg, 93% yield) as an amber color solid. MS (ES+) 329.3 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.06 (s, 1H), 7.48 (s, 1H), 7.22 (t, J=8.54 Hz, 1H), 6.81 (dd, J=8.54, 1.95 Hz, 1H), 6.75 (d, J=11.47 Hz, 1H), 4.52 (q, J=7.16 Hz, 2H), 3.89 (s, 3H), 2.34 (s, 3H), 1.47 (t, J=7.07 Hz, 3H).

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-209875ee459f4ea2974a53d8f007eeab
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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