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

HRID 885253Notes

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

Participants

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

extractionthe mixture was extracted with EtOAc
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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