Water → methyl (Z)-3-[2-butoxy-3'-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate

HRID 390640Notes

Reaction equation

HRID 390640 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH3:20])/[C:15]([O:17][CH3:18])=[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].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH3:20])/[C:15]([O:17][CH3:18])=[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

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 115583693-(3-Heptyl-1-methylureido)phenylboronic acidHCID 59574929methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate

Product 1

HCID 59574928methyl (Z)-3-[2-butoxy-3'-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methoxyacrylateYield 86.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

0.4 g (1 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate prepared as described in Example 24c, 0.4 g (1.33 mmol) of 3-(3-heptyl-1-methylureido)phenylboronic acid and 1 mL (2 mmol) of potassium phosphate are dissolved in 10 mL of dimethylformamide. After bubbling nitrogen through the reaction mixture for 10 minutes, 2 mg (0.01 mmol) of palladium (II) acetate and 7 mg (0.02 mmol) of 2-(dicyclohexylphosphine)biphenyl are added. The reaction mixture is heated at 90° C. for 1 hour 30 minutes with vigorous stirring. After cooling, the reaction is worked up by addition of water and extraction with ethyl acetate. The organic phases are combined, washed with water and with saturated sodium chloride solution and then dried over magnesium sulfate. The solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture to give 0.44 g (85%) of methyl (Z)-3-[2-butoxy-3′-(1-methyl-3-heptylureido)biphenyl-4-yl]-2-methoxyacrylate in the form of an orange oil.

Workup

  1. customAfter bubbling nitrogen through the reaction mixture for 10 minutes
  2. temperatureAfter cooling
  3. washwashed with water and with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvents are evaporated off
  6. customThe crude product obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-bea4d013a6614ada8f41b5ee8ac7a3b6
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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