Dimethylacetamide → 6-Amino-2-(trifluoromethyl)pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-6-(trifluoromethyl)pyridin-2-amine (3.0 g, 12.3 mmol), Zn(CN)2 (0.81 g, 6.9 mmol), Pd2(dba)3 (0.57 g, 0.6 mmol), and Xantphos (0.72 g, 1.2 mmol) in DMA (12 mL) was placed in a sealed tube. The mixture was degassed with argon and stirred at 160° C. for 20 h. The mixture was poured into water and extracted with EtOAc (2×). The combined organic layers were dried over magnesium sulfate and concentrated to dryness. The residue was purified by column chromatography on silica gel eluting with 3:1 EtOAc/hexanes to afford 1.9 g of 6-amino-2-(trifluoromethyl)nicotinonitrile as a solid. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, 1H), 6.67 (d, 1H).

Provenance & Evidence