Potassium Carbonate → 8-bromo-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101301

반응식

HRID 2101301 반응식
[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]1[CH:28]=[N:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=1>CN(C=O)C.O>[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[N:16]([CH2:26][C:27]3[CH:28]=[N:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)[N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 577994388-Bromo-7-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

생성물 1

HCID 577994658-bromo-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of 8-bromo-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (3.24 g, 10.0 mmol) in DMF (15 mL) at room temperature under argon was added K2CO3 (2.76 g, 20.0 mmol) and 3-(chloromethyl)-6-(trifluoromethyl)pyridine (2.34 g, 12.0 mmol). After stirring at room temperature for 3 d, HPLC indicated approximately 70% complete reaction. The mixture was then heated to 60° C. for 5 h, after which HPLC indicated complete reaction. The mixture was cooled to room temperature, diluted with water (100 mL), and stirred for 1 h. Solid was collected by filtration and washed with water (10 mL×5), then methanol (5 mL×2), and finally dried under vacuum. The title compound (4.4 g) was obtained as a yellow solid. HPLC/MS: retention time=3.8 min, [M+H]+=485.

후처리

  1. customapproximately 70% complete reaction
  2. temperatureThe mixture was then heated to 60° C. for 5 h
  3. customreaction
  4. temperatureThe mixture was cooled to room temperature
  5. stirringstirred for 1 h
  6. filtrationSolid was collected by filtration
  7. washwashed with water (10 mL×5)
  8. dry with materialmethanol (5 mL×2), and finally dried under vacuum

출처 및 근거

ORD 기록
ord-ecf84808aae043fcb05910a7512c091f
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572808B2

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