Potassium Carbonate → [4-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

HRID 456196Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10].[CH3:19][O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[CH:25][C:24]=1[O:38][CH3:39].C(=O)([O-])[O-].[K+].[K+]>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>[CH3:19][O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[C:27]([C:2]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=2[CH2:4][N:5]2[CH2:9][CH2:8][O:7][C:6]2=[O:10])[CH:26]=[CH:25][C:24]=1[O:38][CH3:39]

Participants

Conditions

Temperature: 90 °C

Procedure

3-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one (0.085 g, 0.26 mmol), [2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester (0.120 g, 0.39 mmol), potassium carbonate (0.091 g, 0.66 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.030 g, 0.03 mmol) were combined in DME:H2O (2:1; 10 mL), and the mixture was purged with N2. The reaction was stirred at 90° C. for 3 hours, until no starting material was seen by analytical LCMS. After cooling to room temperature, the mixture was worked-up with EtOAc and brine and purified by silica gel chromatography to give the title compound.

Workup

customthe mixture was purged with N2
temperatureAfter cooling to room temperature
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-ff10fd62ab824285aaf8fa919c927d7b
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497381B2

Reaction notes

Loading…