1,2-Dibromoethane → 2-(2-bromoethyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2368024노트

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HRID 2368024 반응식
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16](=[O:19])[NH:17][N:18]=3)[CH:15]=2)=[CH:6][CH:5]=1.[Br:22][CH2:23][CH2:24]Br>CN(C=O)C.O>[Br:22][CH2:23][CH2:24][N:17]1[C:16](=[O:19])[N:14]2[CH:15]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=3)[CH:11]=[CH:12][C:13]2=[N:18]1

참가 물질

5

반응물 2

HCID 78391,2-DibromoethaneHCID 58044589HCID 58044589, 화합물

생성물 1

HCID 580446052-(2-bromoethyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
95 °C

실험 절차

6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (synthesized according to Example 1, 500 mg, 1.69 mmol) was dissolved in 5 ml DMF and 1,2 dibromoethane (1.0 mL, 11.8 mmol) was added. The reaction was heated to 95° C. overnight. The reaction was cooled, diluted with water/EtOAC and the layers were separated. The organic layer was washed with NaHCO3. The organics were dried (MgSO4), filtered, concentrated and purified by flash chromatography (Rf=0.46, 1:1 hexanes:EtOAc) to afford 2-(2-bromoethyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one. To a solution of 2-(2-bromoethyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (50 mg, 0.124 mmol) in 1 mL DMF was added K2CO3 (51 mg, 0.372 mmol) and 4-phenyl-1H-imidazole (36 mg, 0.249 mmol) and the reaction was heated to 85° C. for 24-72 hours until the SM was consumed. The reaction was concentrated and purified by reverse phase HPLC to afford compound 100 (24 mg, 41%). GS-490257. C24H18F3N5O2, m/z (ESI)=466.2 [M+H]+.

후처리

  1. temperatureThe reaction was cooled
  2. customthe layers were separated
  3. washThe organic layer was washed with NaHCO3
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (Rf=0.46, 1:1 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-5e912fbd23b046249414ac0a299207f3
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703759B2

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