N,N'-Dimethylethylenediamine → 6-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57806

반응식

HRID 57806 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu](I)I>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=3)[C:4]=2[CH:3]=1

참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 6394382-Bromo-6-fluoropyridineHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

생성물 1

HCID 862802436-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine수율 55.5%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (13.778 mmol, 2115.9 mg), 2-bromo-6-fluoro-pyridine (15.156 mmol, 2667.3 mg), N,N′-Dimethylethylenediamine (13.778 mmol; 1.215 g; 1.37 mL), Copper iodide (13.778 mmol; 2650.5 mg), and potassium carbonate (15.156 mmol; 2.12 g) in 1,4-Dioxane (10 mL) was purged with Argon, then sealed and stirred at 100° C. for 20 hours. The mixture was cooled to room temperature, and then filtered through Celite. The filtrate was concentrated; the residue was purified on silica and eluted with 0 to 100% Ethyl acetate in Heptane to give 6-Chloro-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine as an off-white solid (1.90 g, 55%) MS (ESI) m/z: 249 [M+H]+

후처리

  1. customwas purged with Argon
  2. customsealed
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified on silica
  7. washeluted with 0 to 100% Ethyl acetate in Heptane

출처 및 근거

ORD 기록
ord-0ae3849eb90847e88320600dde5b5d9f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

연결된 노트

불러오는 중…