Dichloromethane → HCID 70974564, compound

Participants

Reaction Steps

A solution of trimethyl((3-nitrophenyl)ethynyl) silane, (11b) (1.45 g, 6.61 mmol) in DMF (10 mL) was added to the mixture of pentafluoropyridine (1.45 g, 8.59 mmol) and CsF(1.51 g, 9.92 mmol) in DMF (10 mL) slowly. The reaction mixture was stirred overnight. Brine (30 mL) and dichloromethane (60 mL) were added. Organic phase was separated and washed with water (30 mL×3). Solvent was evaporated by rotary evaporation and the residue was chromatographed (Hexane, then EtOAc:Hexane=1:30) to provide the desired product in 72% yield: 1H-NMR (300 MHz, CDCl3) δ 8.49 (dd, J=1.8, 1.8 Hz, 1H), 8.35 (ddd, J=8.4, 2.1, 0.9 Hz, 1H), 7.96 (ddd, J=7.8, 1.2, 1.2 Hz, 1H), 7.66 (dd, J=8.1, 8.1 Hz, 1 H); 13C-NMR (75 MHz, CDCl3) δ 148.2, 143.5 (dm, J=247.6 Hz), 141.9 (dm, J=264.0 Hz), 129.9, 127.0, 125.1, 122.2, 116.3 (tt, J=16.0, 4.4 Hz), 102.9 (t, J=3.5 Hz), 75.2 (t, J=4.2 Hz); HRMS (CI+): calcd for C13H5F4N2O2 [M+H]+ 297.02872, found 297.02908; m.p. 130-131° C.

Provenance & Evidence