Potassium Phosphate, Tribasic → ethyl (Z)-2-ethoxy-3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate

HRID 390672Notes

Reaction equation

HRID 390672 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:34]([O:36][CH2:37][CH2:38][O:39][C:40]1[CH:41]=[C:42](/[CH:47]=[C:48](\[O:54][CH2:55][CH3:56])/[C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH:43]=[CH:44][C:45]=1I)[CH3:35].[CH3:57][N:58]([C:67]1[CH:68]=[C:69](B(O)O)[CH:70]=[CH:71][CH:72]=1)[C:59]([NH:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])=[O:60]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH2:55]([O:54]/[C:48](=[CH:47]\[C:42]1[CH:43]=[CH:44][C:45]([C:69]2[CH:70]=[CH:71][CH:72]=[C:67]([N:58]([CH3:57])[C:59]([NH:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])=[O:60])[CH:68]=2)=[C:40]([O:39][CH2:38][CH2:37][O:36][CH2:34][CH3:35])[CH:41]=1)/[C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH3:56]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 672732723-(1-Methyl-3-pentylureido)phenylboronic acidHCID 68957302ethyl (Z)-3-[3-(2-ethoxyethoxy)-4-iodophenyl]-2-ethoxyacrylate

Product 1

HCID 86626107ethyl (Z)-2-ethoxy-3-[2-(2-ethoxyethoxy)-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylateYield 12%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

29 mg (0.08 mmol) of 2-(dicyclohexylphosphino)biphenyl and 9.3 mg (0.04 mmol) of palladium acetate and then 1.35 mL (2.7 mmol) of aqueous 2 M potassium phosphate solution are added to a solution of 0.9 g (2.07 mmol) of ethyl (Z)-3-[3-(2-ethoxyethoxy)-4-iodophenyl]-2-ethoxyacrylate and 0.58 g (2.5 mmol) of 3-(1-methyl-3-pentylureido)phenylboronic acid (prepared according to Example 24h) in 10 mL of dimethylformamide. The reaction medium 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. After evaporating under vacuum, the residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 100 mg (12%) of ethyl (Z)-2-ethoxy-3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate are obtained.

Workup

  1. washwashed with saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. customAfter evaporating under vacuum
  4. customthe residue obtained
  5. customis purified by chromatography on a column of silica
  6. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-285cfbdcb41a484e97562b3716e33c39
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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