Water → HCID 68957153、化合物

HRID 390650

反応式

HRID 390650 の反応式
I[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1OCCC.[CH3:20][NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.O>CN(C)C=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15]/[C:9](=[CH:8]\[C:5]1[CH:4]=[CH:3][C:2]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:21][CH3:20])[CH:27]=2)=[CH:7][CH:6]=1)/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

7

反応物 3

HCID 962WaterHCID 23558980[3-(Methylamino)phenyl]boronic acidHCID 86626099ethyl (E)-3-(4-iodo-3-propoxyphenyl)-2-methylacrylate

生成物 1

HCID 68957153HCID 68957153、化合物収率 78.7%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 62657Potassium Phosphate, Tribasic溶媒

反応条件

温度
90 °C

実験手順

1.6 g (4.3 mmol) of ethyl (E)-3-(4-iodo-3-propoxyphenyl)-2-methylacrylate are dissolved in 10 mL of a 4/1v/v mixture of dimethylformamide and of aqueous 2 M potassium phosphate solution. 0.9 g (5.7 mmol) of 3-methylaminophenylboronic acid prepared as described in Example 31e, 58 mg (0.2 mmol) of palladium acetate and 152 mg (0.4 mmol) of dicyclohexylbiphenylphosphine are added. The mixture is stirred for 3 hours at 90° C. After cooling and adding water, the medium is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 8/2 heptane/ethyl acetate mixture. 1.0 g (65%) of ethyl (E)-2-methyl-3-(3′-methylaminobiphenyl-4-yl)acrylate is obtained.

後処理

  1. additionare added
  2. temperatureAfter cooling
  3. extractionthe medium is extracted with ethyl acetate
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica
  10. washeluted with an 8/2 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-e1edcaf21acc4dd19f211f0a5f40af81
出典データセット
uspto-grants-2013_02
特許番号
US08383652B2

関連ノート

読み込み中…