Water → methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate

HRID 390692Notes

Reaction equation

HRID 390692 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.[CH2:18]([O:22][C:23]1[CH:24]=[C:25](/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33])[CH:26]=[CH:27][C:28]=1I)[CH2:19][CH2:20][CH3:21].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[NH2:8][C:9]1[CH:10]=[C:11]([C:28]2[CH:27]=[CH:26][C:25](/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33])=[CH:24][C:23]=2[O:22][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27632413-Aminophenylboronic acid hydrochlorideHCID 59574929methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate

Product 1

HCID 86626122methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylateYield 93.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

11.2 mL (22.4 mmol) of aqueous 2 N potassium carbonate solution and 0.52 g (0.45 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 1.87 g (10.8 mmol) of 3-aminophenylboronic acid hydrochloride and 3.5 g (9 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate (prepared according to Example 24c) in 70 mL of ethylene glycol dimethyl ether. The reaction mixture is heated at 100° C. for 4 hours. After addition of 30 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 90/10 heptane/ethyl acetate mixture. 3 g (93%) of methyl (Z)-3-(3′-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate are obtained in the form of a yellow 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 90/10 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-4f9266252fc34994bf2d41c1de451922
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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