Hydrogen Bromide → HCID 58046377、化合物

HRID 2046419ノート

反応式

HRID 2046419 の反応式
[N:1]1[CH:2]=[C:3]([C:10](=[O:12])[CH3:11])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.[BrH:13].[Br:14]Br>C(O)(=O)C>[Br:13][CH:11]([Br:14])[C:10]([C:3]1[N:4]2[N:5]=[CH:6][CH:7]=[CH:8][C:9]2=[N:1][CH:2]=1)=[O:12]

参加物

5

反応物 3

HCID 260Hydrogen Bromide2 回HCID 24408Bromine2 回HCID 450861961-(Imidazo[1,2-b]pyridazin-3-yl)ethan-1-one

生成物 1

HCID 58046377HCID 58046377、化合物

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒3 回

反応条件

温度
60 °C

実験手順

1-(Imidazo[1,2-b]pyridazin-3-yl)ethanone (502 mg, 3.11 mmol) was dissolved in acetic acid (7.8 mL) and 33% HBr in acetic acid (0.564 mL, 3.11 mmol) was added. Bromine (0.177 mL, 3.43 mmol) was added and the solution stirred at 60° C. for 1.5 h. After stirring for 1.5 h, added more bromine (0.08 mL, 1.56 mmol) and 33% HBr in acetic acid (0.282 mL, 1.56 mmol). The solution was stirred at 60° C. for 3 h. The solution was then cooled to room temperature and quenched with 10% aqueous sodium thiosulfate. The aqueous layer was extracted with dichloromethane (×3). The organic layers were combined and washed with aqueous saturated sodium bicarbonate. The organic layer was collected and dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was taken on to the next step without further purification. 1H NMR (500 MHz, CD3SOCD3) δ 8.88 (d, 1H); 8.83 (s, 1H); 8.40 (d, 1H); 7.66 (s, 1H); 7.61 (dd, 1H). LRMS (APCI) calc'd for (C8H5Br2N3O) [M+H]+, 317.9. found 317.9.

後処理

  1. stirringAfter stirring for 1.5 h
  2. stirringThe solution was stirred at 60° C. for 3 h
  3. temperatureThe solution was then cooled to room temperature
  4. customquenched with 10% aqueous sodium thiosulfate
  5. extractionThe aqueous layer was extracted with dichloromethane (×3)
  6. washwashed with aqueous saturated sodium bicarbonate
  7. customThe organic layer was collected
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was taken on to the next step without further purification

出典と根拠

ORDレコード
ord-799c2b2708b940ef9f7e5cb5df7aaa49
出典データセット
uspto-grants-2013_11
特許番号
US08592425B2

反応ノート

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