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

HRID 57806
ノート
印刷プレビュー

反応式

HRID 57806 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717
Copper iodide
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-0ae3849eb90847e88320600dde5b5d9f
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09434725B2

反応ノート

読み込み中…

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