Potassium Carbonate → HCID 58237588, compound

HRID 885370Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][C:14]=2[CH2:20][N:21]2[CH2:25][CH2:24][O:23][C:22]2=[O:26])[CH:7]=1)[CH3:2].[CH3:28][N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.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>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:32]3[CH:31]=[N:30][N:29]([CH3:28])[CH:33]=3)=[CH:15][C:14]=2[CH2:20][N:21]2[CH2:25][CH2:24][O:23][C:22]2=[O:26])[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester (0.1 g, 0.23 mmol), 1-methylpyrazole-4-boronic acid pinacol ester (0.06 g, 0.27 mmol), and potassium carbonate (0.1 g, 0.66 mmol) were combined in DME (3 mL) and H2O (1 mL) and degassed with N2 for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.025 g, 0.022 mmol) was added, and the reaction was stirred at 80° C. for 2 hours to give the title compound, which was directly as a crude solution in the hydrolysis step.

Workup

customH2O (1 mL) and degassed with N2 for 10 minutes

Sources & evidence

ORD record: ord-634b9c59230b4fc697221375378ca1d7
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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