4-(2-Bromo-ethyl)-2,5-diphenyl-oxazole → 2-{1-[2-(2,5-diphenyl-oxazol-4-yl)-ethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol

Participants

Reaction Steps

A solution of 100 mg (0.33 mmol) of 1,1,1,3,3,3-hexafluoro-2-(2-methyl-2,3-dihydro-1H-indol-5-yl)-propan-2-ol (example 51.1) and 4-(2-bromo-ethyl)-2,5-diphenyl-oxazole in 0.5 mL of DMF was stirred at 80° C. overnight. Distribution of the mixture between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with n-heptane/EtOAc 4:1 yielded 39 mg (21%) of 2-{1-[2-(2,5-diphenyl-oxazol-4-yl)-ethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol, light yellow gum, MS: 547 (MH+).

Provenance & Evidence