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

HRID 390643Notes

Reaction equation

HRID 390643 reaction equation
[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].[CH2:21]([NH:28][C:29](=[O:41])[N:30]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)[CH3:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].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:34]1[CH:35]=[CH:36][CH:37]=[C:32]([N:30]([CH3:31])[C:29]([NH:28][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:41])[CH:33]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 115583693-(3-Heptyl-1-methylureido)phenylboronic acidHCID 68961569(Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylic acid

Product 1

HCID 16224624(Z)-3-[2-butoxy-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylic acidYield 23.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

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-(3-heptyl-1-methylureido)phenylboronic acid prepared as described in Example 25b are dissolved in 4 mL of a 75/25 solution of ethylene glycol dimethyl ether/water. After addition of 0.2 mL (1.1 mmol) of aqueous 2 M potassium carbonate solution, 0.004 mg (0.005 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium are 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. 60 mg (23%) of (Z)-3-[2-butoxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylic acid are obtained in the form of a beige-colored solid with a melting point of 103° C.

Workup

  1. customprepared
  2. additionare added
  3. extractionthe reaction medium is extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium 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, 7/3

Sources & evidence

ORD record
ord-f27426b5f3c242c59ab9c4eb6af690fe
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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