{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid → {3-[4-Ethylcarbamoyl-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid

HRID 885252Notes

Reaction equation

Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[C:4]([CH2:19][N:20]2[CH2:24][CH2:23][O:22][C:21]2=[O:25])[CH:3]=1>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(N)C>[CH2:19]([NH:20][C:21]([C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[C:4]([CH2:19][N:20]2[CH2:24][CH2:23][O:22][C:21]2=[O:25])[CH:3]=1)=[O:22])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid (0.2 g, 0.49 mmol) and ethylamine (2M in THF; 10 mL) were combined in a sealed tube and flushed with carbon monoxide for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.057 g, 0.05 mmol) was added, and the solution was flushed with carbon monoxide for 10 minutes. The tube was sealed and heated to 100° C. overnight. The crude mixture was purified by preparative HPLC to give the desired product.

Workup

customflushed with carbon monoxide for 5 minutes
customthe solution was flushed with carbon monoxide for 10 minutes
customThe tube was sealed
customThe crude mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-7a915dd0c24c4177b2f876bda4c5d44b
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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