Cesium carbonate → 7-chloro-2-(difluoromethyl)-2H-pyrazolo[3,4-c]pyridine

HRID 930478노트

반응식

HRID 930478 반응식
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[N:9][NH:8][C:7]=12.Cl[C:12]([F:17])([F:16])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[C:7]2=[N:8][N:9]([CH:12]([F:17])[F:16])[CH:10]=[C:6]2[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 126684917-Chloro-1H-pyrazolo[3,4-c]pyridine

생성물 1

HCID 867322847-chloro-2-(difluoromethyl)-2H-pyrazolo[3,4-c]pyridine수율 21.34%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
95 °C

실험 절차

A mixture of 7-chloro-1H-pyrazolo[3,4-c]pyridine (4.99 g, 32.5 mmol), sodium chlorodifluoroacetate (14.86 g, 97 mmol), and cesium carbonate (40.2 g, 123 mmol) in DMF (81 ml) was heated at 95° C. for 4 h. The reaction was allowed to cool to rt and the solids were filtered. The filtrate was diluted with water and extracted with EtOAc. The organic extract was washed with water, satd NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (100 g), eluting with a gradient of 5% to 60% EtOAc in hexane, to provide a white solid (1.4117 g, 6.93 mmol, 21.34% yield). MS m/z=203.9 [M+H]+. Calculated for C7H4ClF2N3: 203.

후처리

  1. temperatureto cool to rt
  2. filtrationthe solids were filtered
  3. additionThe filtrate was diluted with water
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customchromatographed through a Biotage SNAP HP-silica gel column (100 g)
  11. washeluting with a gradient of 5% to 60% EtOAc in hexane

출처 및 근거

ORD 기록
ord-4ca554dc963e4db29d430d247b0bde85
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296734B2

반응 노트

불러오는 중…