Dimethylformamide → HCID 86623738, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[[4-bromo-2-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethanol (0.699 g, 1.92 mmol) and Zn(CN)2 (0.157 g, 1.34 mmol) in DMF (5 mL) was sparged with N2 for 15 min at rt and Pd(PPh3)4 (0.111 g, 0.096 mmol) was added in one portion, taking care not to allow air into the reaction flask. The mixture was heated to 80° C. under N2 for 40 min, cooled, poured into dilute NH4OH, and the whole was extracted with Et2O (×3). The combined organic portions were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.571 g of the title compound as a colorless gum: 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=1.6 Hz, 1H), 7.82 (dd, J=8.4, 1.8 Hz, 1H), 7.56 (d, J=8.6 Hz, 1H), 3.86 (q, J=8.9 Hz, 2H), 3.69 (t, J=2H), 3.50 (t, J=5.2 Hz, 2H), 1.74 (bs, 1H).

Provenance & Evidence