Stannous Chloride → HCID 86673523, compound

Participants

Reaction Steps

SnCl2 (3.26 g, 17.2 mmol) was added to the solution of 2,3,5,6-tetrafluoro-4-((2-nitrophenyl)ethynyl) pyridine, (12c) (1.02 g, 3.44 mmol) in EtOH (100 mL). The reaction mixture was refluxed for 1.5 hours. After basification till pH>9 with NaOH (1.0 N solution), the product was extracted with dichloromethane. Solvent was evaporated and 0.22 g (24%) of the product aniline was purified by recrystallization with benzene. The residue was purified by column chromatography on silica gel using EtOAc:Hexane=1:10 as the eluent to yield the product (0.53 g, 68%): 1H-NMR (300 MHz, acetone-d6) δ 7.39 (d, J=7.5 Hz, 1H), 7.26 (ddd, J=8.4, 6.9, 1.5 Hz, 1H), 6.89 (d, J=8.4 Hz, 1H), 6.69 (ddd, J=7.5, 7.5, 1.2 Hz, 1H), 5.35 (s, 2H); 13C-NMR (150 MHz, CDCl3) δ 149.3, 143.7 (dm, J=245.3 Hz), 141.4 (dm, J=260.9 Hz), 133.0, 132.6, 118.3, 117.8 (m), 114.8, 104.7, 104.6 (t, J=3.5 Hz), 79.4 (t, J=4.3 Hz); HRMS (ESI+): calcd for C13H7F4N2 [M +H]+ 267.05454, found 267.05454; m.p. 133-134° C.

Provenance & Evidence