Water → methyl (Z)-2-Ethoxy-3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate

HRID 390674Notes

Reaction equation

HRID 390674 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([O:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17](/[CH:22]=[C:23](\[O:28][CH3:29])/[C:24]([O:26][CH3:27])=[O:25])[CH:18]=[CH:19][C:20]=1I)[CH3:10].[CH3:30][N:31]([C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=1)[C:32]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:33].O.[CH3:50]N(C)C=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C(OCC)(=O)C>[CH2:29]([O:28]/[C:23](=[CH:22]\[C:17]1[CH:18]=[CH:19][C:20]([C:44]2[CH:43]=[CH:42][CH:41]=[C:40]([N:31]([CH3:30])[C:32]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:33])[CH:45]=2)=[C:15]([O:14][CH2:13][CH2:12][O:11][CH2:9][CH3:10])[CH:16]=1)/[C:24]([O:26][CH3:27])=[O:25])[CH3:50]

Participants

9

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 672732723-(1-Methyl-3-pentylureido)phenylboronic acidHCID 86626108methyl (Z)-3-[3-(2-ethoxyethoxy)-4-iodophenyl]-2-methoxyacrylate

Product 1

HCID 86626111methyl (Z)-2-Ethoxy-3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylateYield 89%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

6.9 mg (0.02 mmol) of 2-(dicyclohexylphosphino)biphenyl and 2.2 mg (0.01 mmol) of palladium acetate and then 0.32 mL (0.64 mmol) of aqueous 2 M potassium phosphate solution are added to a solution of 200 mg (0.49 mmol) of methyl (Z)-3-[3-(2-ethoxyethoxy)-4-iodophenyl]-2-methoxyacrylate and 0.65 g (2.5 mmol) of 3-(1-methyl-3-pentylureido)phenylboronic acid (prepared according to Example 24h) in 10 mL of dimethylformamide. The reaction mixture is heated at 90° C. for 3 hours. After addition of 20 mL of water and extraction with ethyl acetate, the organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 217.8 mg (89%) of methyl (Z)-2-Ethoxy-3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate are obtained in the form of an orange oil.

Workup

  1. washwashed with saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then purified by chromatography on a column of silica
  5. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-e48eb3b1b5d94900a71be9b2c2d64cb5
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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