Toluene → 4-[(2-{[4-(1,3-Thiazol-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[(2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.100 g, 0.19 mmol; step A above), 2-bromothiazole (0.020 mL, 0.21 mmol), Pd(PPh3)4 (0.011 g, 0.010 mmol), Na2CO3 (0.106 g, 1.00 mmol), toluene (1 mL), EtOH (0.50 mL) and H2O (0.5 mL) was sparged with N2 for 10 min and then heated at 80° C. in a sealed vial for 72 h. The mixture was cooled, poured into water, and extracted with EtOAc (×3). Combined organics were washed (H2O, brine), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.0059 g of the title compound as a yellow film: MS (ESI) m/z 472 (M+1).

Provenance & Evidence