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Potassium Carbonate → {3-[3-(2-Oxo-oxazolidin-3-ylmethyl)-biphenyl-4-yloxy]-phenyl}-acetic acid methyl ester

HRID 885253
Notes
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Reaction equation

HRID 885253 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][C:13]=2[CH2:19][N:20]2[CH2:24][CH2:23][O:22][C:21]2=[O:25])[CH:6]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>COCCOC.O.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>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:14][C:13]=2[CH2:19][N:20]2[CH2:24][CH2:23][O:22][C:21]2=[O:25])[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 66827Phenylboronic AcidHCID 58237622{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester

Product 1

HCID 58237560{3-[3-(2-Oxo-oxazolidin-3-ylmethyl)-biphenyl-4-yloxy]-phenyl}-acetic acid methyl esterYield 29.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester (0.1 g, 0.24 mmol), phenylboronic acid (0.044 g, 0.36 mmol), tetrakis(triphenylphosphine)palladium(0) (0.027 g, 0.02 mmol), and potassium carbonate (0.082 g, 0.59 mmol) were combined in DME:H2O (2:1; 3 mL) and stirred at 90° C. for 5 hours. Once no starting material was seen by analytical LCMS, the pH was adjusted to pH 7 with saturated aqueous NH4Cl, and the mixture was extracted with EtOAc. The crude material was purified by silica gel chromatography to give the desired product (0.03 g).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f5a73d3fda7a4197bea25831b26cb085
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242145B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes