(3-Chlorophenyl)boronic acid → HCID 59831833, compound

HRID 1716650Notes

Reaction equation

HRID 1716650 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1>O.O1CCOCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)[C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:16])[CH:22]=1

Participants

5

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 54059723HCID 54059723, compound

Product 1

HCID 59831833HCID 59831833, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-(1H-indol-6-yl)-acrylic acid methyl ester XXX (0.4 g, 2.0 mmol), 3-chlorophenyl boronic acid (0.62 g, 4.0 mmol), [RhCl(cod)]2 (49 mg, 0.10 mmol) and TEA (0.42 ml, 3.0 mmol) in water (6 ml) and 1,4-dioxane (1 ml) was stirred at 95° C. for 18 hours. The reaction mixture was cooled to room temperature, and partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) to provide 3-(1H-indol-6-yl)-3-(3-chloro-phenyl)-propionic acid methyl ester XL (90 mg, 62% yield) as a white foam.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between H2O and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-25e52a90d6e2479693f6c04cd81a08c3
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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