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Cesium carbonate → methyl 4-((4,4,4-trifluoro-1-(2-methyl-4-(4,5,6,7-tetrahydro-2H-indazol-2-yl)phenyl)butyl)amino)benzoate

HRID 1520281
ノート
印刷プレビュー

反応式

HRID 1520281 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:26])[CH:3]=1.[NH:27]1[C:35]2[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=2[CH:29]=[N:28]1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I.O.C1(C)C=CC=CC=1>[F:12][C:11]([F:14])([F:13])[CH2:10][CH2:9][CH:8]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)[C:5]1[CH:6]=[CH:7][C:2]([N:28]2[CH:29]=[C:30]3[C:35]([CH2:34][CH2:33][CH2:32][CH2:31]3)=[N:27]2)=[CH:3][C:4]=1[CH3:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 753174,5,6,7-tetrahydro-1H-indazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 117840148Methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate

生成物 1

HCID 117840555methyl 4-((4,4,4-trifluoro-1-(2-methyl-4-(4,5,6,7-tetrahydro-2H-indazol-2-yl)phenyl)butyl)amino)benzoate

試薬・触媒・溶媒

3
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

Under a nitrogen atmosphere, a mixture of methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate (optically active form, compound with longer retention time) (3.0 g), 4,5,6,7-tetrahydroindazole (1.278 g), copper(I) iodide (1.594 g), trans-N,N′-dimethylcyclohexane-1,2-diamine (2.64 mL), cesium carbonate (6.82 g) and toluene (17.4 mL) was stirred at 110° C. for 18 hr. To the reaction mixture was added water at room temperature, and the insoluble material was filtered off through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.11 g).

後処理

  1. filtrationthe insoluble material was filtered off through celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-079aeec6728345b9a5a2363b7216c68a
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073864B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート