Potassium Carbonate → 6-Cyclopropyl-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 6-bromo-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine (step 3) (200 mg, 0.346 mmol) in dry 1,4-dioxane (10 ml) under N2 at RT was added K2CO3 (144 mg, 1.039 mmol) followed by cyclopropylboronic acid (89 mg, 1.039 mmol) and palladiumtetrakis (40.0 mg, 0.035 mmol). The resulting suspension was stirred and heated at reflux (120° C.) overnight for 4 days. The mixture was filtered through Celite® (filter material) and washed through with water (30 ml) and EtOAc (50 ml). The filtrate was separated and the organic portion was dried (MgSO4) and concentrated in vacuo to afford the title compound which was used in the next step without further purification; LC-MS Rt=7.75 min [M+H]+ 539.6 Method 10minLC_v003.

Provenance & Evidence