Bromine → 5-bromo-1H-indazole-3-carboxylic Acid

HRID 2367693ノート

反応式

HRID 2367693 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.[Br:13]Br>C(O)(=O)C>[Br:13][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[C:3]2[C:10]([OH:12])=[O:11]

参加物

4

反応物 2

HCID 24408BromineHCID 78250Indazole-3-carboxylic acid

生成物 1

HCID 71573585-bromo-1H-indazole-3-carboxylic Acid収率 87.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
120 °C

実験手順

A suspension of indazole-3-carboxylic acid (CX) (1.0 g, 6.16 mmol) in glacial acetic acid (60 mL) was heated at 120° C. to get a clear solution. The solution was cooled to 90° C. A solution of bromine (0.633 mL, 12.33 mmol) in glacial acetic acid (2 mL) was added slowly to the solution while heating at 90° C. The solution was further heated 16 h at 90° C. The solution was cooled to room temperature, poured into ice water and further stirred at room temperature for 15 min The solids formed were filtered, washed with cold water and dried under vacuum at room temperature to get 5-bromo-1H-indazole-3-carboxylic acid (CXV) as a white solid (1.30 g, 5.39 mmol, 87.5% yield). 1H NMR (DMSO-d6) δ ppm 13.95 (s, 1H), 13.18 (br s, 1H), 8.21 (d, J=1.2 Hz, 1H), 7.65 (d, J=7.0 Hz, 1H), 7.56 (dd, J=7.0, 1.2 Hz, 1H); ESIMS found for C8H4BrN2O2 m/z 242.0 (M+H).

後処理

  1. customto get a clear solution
  2. temperatureThe solution was cooled to 90° C
  3. temperaturewhile heating at 90° C
  4. temperatureThe solution was cooled to room temperature
  5. customformed
  6. filtrationwere filtered
  7. washwashed with cold water
  8. customdried under vacuum at room temperature

出典と根拠

ORDレコード
ord-edbfe5c552f5488b956bc2d2d8a01151
出典データセット
uspto-grants-2014_04
特許番号
US08697887B2

反応ノート

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