Stannous Chloride → HCID 86673521, compound

Participants

Reaction Steps

SnCl2 (3.94 g, 20.8 mmol) was added to the solution of 2,3,5,6-tetrafluoro-4-((3-nitrophenyl)ethynyl) pyridine, (12b) (1.23 g, 4.15 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 0.73 g (66%) of the product aniline was purified by recrystallization with benzene. The residue was purified by column chromatography on silica gel using EtOAc:Hexane=1:5 as the eluent to yield the product (0.37 g, 33%): 1H-NMR (300 MHz, CDCl3) δ 7.21 (dd, J=7.2, 7.2 Hz, 1H), 7.03 (d, J=7.5 Hz, 1H), 6.93 (s, 1H), 6.79 (dd, J=7.4, 1.5 Hz, 1H), 3.80 (s, 2H); 13C-NMR (150 MHz, CDCl3) δ 146.7, 143.6 (dm, J=241.8 Hz), 142.0 (dm, J=262.4 Hz), 129.8, 122.8, 121.4, 118.2, 117.7 (m), 117.6, 107.4 (t, J=3.8 Hz), 72.9 (t, J=4.3 Hz); HRMS (ESI+): calcd for C13H7F4N2 [M+H]+ 267.05454, found 267.05405; m.p. 172-173° C.

Provenance & Evidence