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

HRID 390632노트

반응식

HRID 390632 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2962060984d54387b66b7f18dea842b4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383652B2

반응 노트

불러오는 중…