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

HRID 1373829노트

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HRID 1373829 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-4c47396b13664a9baac4e892a6e4db54
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163940B2

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