Cesium carbonate → 4-{4-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy}benzoic acid

HRID 2359322Notes

Reaction equation

I[C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[C:23](B(O)O)=[CH:22][C:21]([C:27]([F:30])([F:29])[F:28])=[N:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[CH3:18][N:19]1[C:23]([C:2]2[CH:17]=[CH:16][C:5]([O:6][C:7]3[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=3)=[CH:4][CH:3]=2)=[CH:22][C:21]([C:27]([F:30])([F:29])[F:28])=[N:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 4-(4-iodophenoxy)benzoic acid (Preparation 143, 470 mg, 1.38 mmol), 1-methyl-3-trifluoromethylpyrazole-5-boronic acid (322 mg, 1.66 mmol), palladium tetrakis triphenyl phosphine (239 mg, 0.207 mmol) and cesium carbonate (1.35 g, 4.15 mmol) in dioxane/water (10 mL/5 mL) was heated to 80° C. for 6 hours then left to stir at room temperature overnight. The reaction was quenched by the addition of 1N HCl and extracted into ethyl acetate. The organic layer was collected, dried over magnesium sulfate and concentrated in vacuo to furnish the crude title compound that was taken on directly to the next step.

Workup

waitthen left
customThe reaction was quenched by the addition of 1N HCl
extractionextracted into ethyl acetate
customThe organic layer was collected
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a7cd7bd2baeb4c1d8dbb2fc49d0855f9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685977B2

Reaction notes

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