Potassium Carbonate → [2'-(1-Ethyl-3-methyl-ureidomethyl)-5,4'-bis-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

HRID 563553Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7](OS(C(F)(F)F)(=O)=O)[CH:6]=1.[CH2:24]([N:26]([CH2:31][C:32]1[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:33]=1B1OC(C)(C)C(C)(C)O1)[C:27]([NH:29][CH3:30])=[O:28])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>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.COCCOC>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:6]=[C:7]([C:33]2[CH:34]=[CH:35][C:36]([C:38]([F:41])([F:39])[F:40])=[CH:37][C:32]=2[CH2:31][N:26]([CH2:24][CH3:25])[C:27]([NH:29][CH3:30])=[O:28])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(3-Trifluoromethanesulfonyloxy-5-trifluoromethyl-phenyl)-acetic acid methyl ester (0.063 g, 0.18 mmol), 1-ethyl-3-methyl-1-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-urea (0.070 g, 0.18 mmol, potassium carbonate (0.062 g, 0.45 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.021 g, 0.02 mmol) were combined in 2:1 DME:H2O (3 mL) and degassed with N2 for 10 minutes. The reaction was then stirred at 90° C. for 2 hours, until no starting material was seen by analytical LCMS. The mixture was cooled to room temperature and used directly in the hydrolysis step.

Workup

customH2O (3 mL) and degassed with N2 for 10 minutes
temperatureThe mixture was cooled to room temperature
customused directly in the hydrolysis step

Sources & evidence

ORD record: ord-8ff9b376626649b09ffb612ed275bd84
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067445B2

Reaction notes

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