Water → HCID 178499173、化合物

HRID 62083ノート

反応式

HRID 62083 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.C([O-])(=O)C.[Na+].[Br:19]Br.O>C(O)(=O)C>[Br:19][C:8]1[CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2][NH:1][C:5]2=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 178499174HCID 178499174、化合物

生成物 1

HCID 178499173HCID 178499173、化合物収率 31%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
120 °C

実験手順

A mixture of methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VI) (0.177 g, 1 mmol), sodium acetate (0.492 g, 6 mmol) and bromine (0.308 mL, 6 mmol) in glacial acetic acid (5 mL) was heated overnight at 120° C. in a sealed tube. The solution was cooled and poured into water. The solids formed were filtered, washed with water and dried at room temperature under vacuum. The crude product was purified on a flash silica gel column (100% DCM→100:2 DCM:MeOH) to produce methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VII) as a white solid (78 mg, 0.31 mmol, 30% yield). 1H NMR (CDCl3) δ ppm 3.95 (s, 3H), 8.62 (d, J=3.01 Hz, 1H), 8.73 (d, J=3.01 Hz, 1H); ESIMS found for C8H6BrN3O2 m/z 256.3 (M+H).

後処理

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried at room temperature under vacuum
  6. customThe crude product was purified on a flash silica gel column (100% DCM→100:2 DCM:MeOH)

出典と根拠

ORDレコード
ord-da7d7862aeda4746bfbdc583ff1ac005
出典データセット
uspto-grants-2016_09
特許番号
US09446035B2

反応ノート

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