Water → (Z)-3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-ethoxyacrylic acid

HRID 390642ノート

反応式

HRID 390642 の反応式
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:18][CH2:19][CH3:20])/[C:15]([OH:17])=[O:16])[CH:9]=[CH:10][C:11]=1I)[CH2:2][CH2:3][CH3:4].[CH3:21][N:22]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:24].C(=O)([O-])[O-].[K+].[K+].O>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:18][CH2:19][CH3:20])/[C:15]([OH:17])=[O:16])[CH:9]=[CH:10][C:11]=1[C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([N:22]([CH3:21])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:24])[CH:32]=1)[CH2:2][CH2:3][CH3:4]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 672732723-(1-Methyl-3-pentylureido)phenylboronic acidHCID 68961569(Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylic acid

生成物 1

HCID 16224623(Z)-3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-ethoxyacrylic acid収率 20.7%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

0.2 g (0.5 mmol) of (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylic acid prepared as described in Example 23a and 0.2 g (0.6 mmol) of 3-(1-methyl-3-pentylureido)phenylboronic acid prepared as in Example 24h are dissolved in 4 mL of a 75/25 solution of ethylene glycol dimethyl ether/water. After addition of 0.2 mL (1.2 mmol) of aqueous 2M potassium carbonate solution, 0.004 mg (0.005 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium is added and the reaction medium is heated at 80° C. for 18 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 8/2, 7/3 and then 5/5 heptane/ethyl acetate mixture. 50 mg (20%) of (Z)-3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]-2-ethoxyacrylic acid are obtained in the form of a beige-colored solid with a melting point of 59° C.

後処理

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

出典と根拠

ORDレコード
ord-11d621d6c684462f84e2cc465ff05144
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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