Water → methyl (Z)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)-2-ethoxyacrylate

HRID 390632ノート

反応式

HRID 390632 の反応式
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH2:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1I)[CH2:2][CH2:3][CH3:4].[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH2:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1[C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([NH:23][CH3:22])[CH:25]=1)[CH2:2][CH2:3][CH3:4]

参加物

7

反応物 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86626090methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylate

生成物 1

HCID 86626091methyl (Z)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)-2-ethoxyacrylate収率 63%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 0.4 g (1 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylate in 8 mL of ethylene glycol dimethyl ether placed under nitrogen, 0.25 g (1.1 mmol) of methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]amine (prepared as in Example 10a), 1.5 mL (3 mmol) of aqueous 2 M potassium phosphate solution, 2 mg (0.01 mmol) of palladium (II) acetate and 7 mg (0.02 mmol) of dicyclohexyl-o-biphenylphosphine are added. The reaction medium is then heated at 80° C. for 20 hours. After addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 85/15 heptane/ethyl acetate mixture. 0.2 g (63%) of methyl (Z)-3-(2-butoxy-3′-methylaminobiphenyl-4-yl)-2-ethoxyacrylate are obtained.

後処理

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with an 85/15 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-2962060984d54387b66b7f18dea842b4
出典データセット
uspto-grants-2013_02
特許番号
US08383652B2

反応ノート

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