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

HRID 268780
Notes
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Reaction equation

HRID 268780 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-514bce0ce6094f258bffd68a1234e166
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07446118B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes