(Diethylamino)sulfur trifluoride → HCID 71059681, compound

Participants

Reaction Steps

To 3-(4-(4-nitropyridin-3-yl)phenyl)propan-1-ol (60 mg, 0.23 mmol) in 2 mL of dry DCM at 0° C. was added (Diethylamino)sulfur trifluoride (111 mg, 0.69 mmol) dropwise. The reaction was warmed to rt and stirred for 1 h and quenched onto ice (20 g) in saturated Na2CO3 (20 mL). The mixture was extracted with EtOAc (2×30 mL) and the organic phase was dried over MgSO4 and concentrated. The residue was purified by silica chromatography (EtOAc in hexane, 5% to 30%) to afford 3-(4-(3-fluoropropyl)phenyl)-4-nitropyridine as a pale-yellow oil (12 mg, 20%). 1H NMR (400 MHz, CDCl3): δ 8.82-8.80 (m, 2H), 7.64 (d, J=5.2, 1H), 7.33-7.27 (m, 2H), 4.55 (t, J=5.6 Hz, 1H), 4.43 (t, J=5.6 Hz, 1H), 2.82 (t, J=7.6 Hz, 2H), 2.12-1.99 (m, 2H); MS (ESI) m/z [M+H]+261.

Provenance & Evidence