Chlorosuccinimide → 7-Chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine

HRID 1373829ノート

反応式

HRID 1373829 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.[Cl:28]N1C(=O)CCC1=O>O1CCCC1.CCOCC>[Cl:28][C:15]1[N:10]2[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:16]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[C:11]2[CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 31398ChlorosuccinimideHCID 98571462-(4-Fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridineHCID 178418339Butyllithium

生成物 1

HCID 98584077-Chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine収率 71%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine (100 mg, 0.346 mmol) in 4 ml of tetrahydrofuran at −78° C. under N2 was added 2.5 M n-butyllithium in hexanes (22 μl, 2 eq). The mixture was stirred at −78° C. for 30 min and N-chlorosuccinimide (2.2 eqv) was then added. The mixture was allowed to warm to room temperature after 30 min and was stirred at room temperature for 1 hr. The mixture was diluted with ether and washed with 1N hydrochloric acid solution. The aqueous layer was basified with 1N sodium hydroxide solution and extracted thoroughly with ether. The combined organic layers were dried on anhydrous magnesium sulfate, filtered and evaporated. Purification by chromatography yielded 7-chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine (71%).

後処理

  1. temperatureto warm to room temperature after 30 min
  2. stirringwas stirred at room temperature for 1 hr
  3. washwashed with 1N hydrochloric acid solution
  4. extractionextracted thoroughly with ether
  5. dry with materialThe combined organic layers were dried on anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography

出典と根拠

ORDレコード
ord-4c47396b13664a9baac4e892a6e4db54
出典データセット
uspto-grants-2007_01
特許番号
US07163940B2

反応ノート

読み込み中…