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

HRID 390642노트

반응식

HRID 390642 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

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

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11d621d6c684462f84e2cc465ff05144
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383652B2

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