Sodium Iodide → 1,1,1,3,3,3-Hexafluoro-2-(4-(((5-methyl-2-(3-(trifluoromethyl)phenyl)oxazol-4-yl)methyl)(2,2,2-trifluoroethyl)amino)phenyl)propan-2-ol

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Reaction Steps

A mixture of 100 mg (0.29 mmol) of 1,1,1,3,3,3-hexafluoro-2-[4-(2,2,2-trifluoro-ethylamino)-phenyl]-propan-2-ol (example 11.2), of 81 mg (0.29 mmol) 4-chloromethyl-5-methyl-2-(3-trifluoromethyl-phenyl)-oxazole and ca 10 mg of NaI in DMF was stirred for 1 week at 125° C. and then distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with a gradient of n-heptane/EtOAc gave 2 mg (ca. 1%) of 1,1,1,3,3,3-hexafluoro-2-{4-[[5-methyl-2-(3-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-(2,2,2-trifluoro-ethyl)-amino]-phenyl}-propan-2-ol, yellow solid, MS: 581 (MH+).

Provenance & Evidence