Water → methyl (Z)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)-2-ethoxyacrylate

HRID 390632Notes

Reaction equation

HRID 390632 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH2:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1I)[CH2:2][CH2:3][CH3:4].[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:19][CH2:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][C:11]=1[C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([NH:23][CH3:22])[CH:25]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86626090methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylate

Product 1

HCID 86626091methyl (Z)-3-(2-butoxy-3'-methylaminobiphenyl-4-yl)-2-ethoxyacrylateYield 63%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.4 g (1 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylate in 8 mL of ethylene glycol dimethyl ether placed under nitrogen, 0.25 g (1.1 mmol) of methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]amine (prepared as in Example 10a), 1.5 mL (3 mmol) of aqueous 2 M potassium phosphate solution, 2 mg (0.01 mmol) of palladium (II) acetate and 7 mg (0.02 mmol) of dicyclohexyl-o-biphenylphosphine are added. The reaction medium is then heated at 80° C. for 20 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 85/15 heptane/ethyl acetate mixture. 0.2 g (63%) of methyl (Z)-3-(2-butoxy-3′-methylaminobiphenyl-4-yl)-2-ethoxyacrylate are obtained.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with an 85/15 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-2962060984d54387b66b7f18dea842b4
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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