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

HRID 1054803ノート

反応式

HRID 1054803 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-209875ee459f4ea2974a53d8f007eeab
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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