Potassium Acetate → 7-Chloro-1H-pyrazolo[3,4-c]pyridine

HRID 930477ノート

反応式

HRID 930477 の反応式
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].C([O-])(=O)C.[K+].[N:15]([O-])=O.[Na+]>CC(O)=O.O>[Cl:9][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[CH:8]=[N:15][NH:1][C:2]=12

参加物

6

反応物 3

HCID 517044Potassium AcetateHCID 27563873-Amino-2-chloro-4-methylpyridineHCID 23668193Sodium Nitrite

生成物 1

HCID 126684917-Chloro-1H-pyrazolo[3,4-c]pyridine収率 46%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a cooled (internal temperature of <13° C.) mixture of 3-amino-2-chloro-4-methylpyridine (10.14 g, 71.1 mmol, Matrix) and potassium acetate (9.02 g, 92 mmol) in AcOH (200 mL) was added a solution of sodium nitrite (7.36 g, 107 mmol) in water (30 mL) dropwise while maintaining an internal temperature <13° C. The reaction was allowed to warm slowly to rt and stirred for 66 h. The mixture was concentrated under reduced pressure and the residue was basified with saturated NaHCO3. The solid was filtered and washed with water. The solid was stirred over EtOAc overnight and filtered. The filtrate was combined with the organic extracts, evaporated onto silica gel and purified by flash chromatography (Isco (120 gram)) eluting with EtOAc:hexanes (0:1→1:1) to give a white crystalline solid (4.99 g, 46%). MS m/z=153.9, 155.9 [M+H]+. Calculated for C6H4ClN3: 153.

後処理

  1. temperatureTo a cooled
  2. temperaturewhile maintaining an internal temperature <13° C
  3. concentrationThe mixture was concentrated under reduced pressure
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. stirringThe solid was stirred over EtOAc overnight
  7. filtrationfiltered
  8. customevaporated onto silica gel
  9. custompurified by flash chromatography (Isco (120 gram))
  10. washeluting with EtOAc:hexanes (0:1→1:1)

出典と根拠

ORDレコード
ord-8e111b8d57484b07abf4439c4212211a
出典データセット
uspto-grants-2016_03
特許番号
US09296734B2

反応ノート

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