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

HRID 929788

反応式

HRID 929788 の反応式
[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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4ffa20c1ded541249e1834712c4d64e6
出典データセット
uspto-grants-2016_03
特許番号
US09296711B2

関連ノート

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