Cesium carbonate → Methyl 2-fluoro-4-({4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)benzoate

HRID 1257465Notes

Reaction equation

I[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:7]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O>[F:18][C:19]1[CH:20]=[C:21]([CH2:2][C:3]2[S:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)[N:7]=2)[CH:22]=[CH:23][C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

Conditions

Temperature: 90 °C

Procedure

Under a nitrogen atmosphere, to a mixed solvent of the compound (270 mg, 0.72 mmol) obtained in Example 190c, 3-fluoro-4-methoxycarbonylphenylboronic acid (170 mg, 0.86 mmol) and cesium carbonate (1.2 g, 3.6 mmol) in tetrahydrofuran-water (v/v=5/1, 6 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (120 mg, 0.14 mmol), and the mixture was stirred at 90° C. overnight. The resulting salt was filtered and removed, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=75/25) to give the title compound as colorless crystals.

Workup

filtrationThe resulting salt was filtered
customremoved
customthe solvent was evaporated under reduced pressure
customThe obtained crude product
customwas purified by column chromatography (hexane-hexane/ethyl acetate=75/25)

Sources & evidence

ORD record: ord-ccd1fc2be8874aeab2b31744999cc4fb
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461348B2

Reaction notes

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