Potassium Carbonate → 3-[4-(2-Trifluoromethyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide

HRID 929788

반응식

HRID 929788 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH2:15])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([F:33])([F:32])[F:31]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:31][C:30]([F:32])([F:33])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH2:15])=[O:14])[O:10][N:9]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide2회

생성물 1

HCID 762807973-[4-(2-Trifluoromethyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide수율 2%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

3-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 2; 40 mg, 0.196 mmol) was dissolved in DMF (1 mL). K2CO3 (19 mg, 0.14 mmol), tetrabutylammonium iodide (7 mg, 0.02 mmol), and 1-chloromethyl-2-trifluoromethyl-benzene (36 μL, 0.25 mmol) were added. The reaction mixture was heated at 40° C. for 14 h. The reaction mixture was partitioned between H2O (5 mL) and EtOAc (5 mL). The organic layer was dried (Na2SO4), filtered, evaporated, and purified by chromatography (30% EtOAc/hexanes) to give 3-[4-(2-trifluoromethyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (1.3 mg, 2%) as a white solid. HRMS Calcd. for C18H14F3N2O3 (M+H)+, 363.0951. Found: 363.0950.

후처리

  1. customThe reaction mixture was partitioned between H2O (5 mL) and EtOAc (5 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by chromatography (30% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-4ffa20c1ded541249e1834712c4d64e6
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296711B2

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