Sodium Azide → HCID 70981929, compound

Participants

Reaction Steps

3-(6-(Chloromethyl)pyridazin-3-yl)-4-fluoro-N,N-dimethylbenzamide (470 mg, 1.60 mmol) was treated with NaN3 (312 mg, 4.80 mmol) and DMF (5 mL) and stirred at RT for 15 h. The reaction mixture was extracted with EtOAc and the organic layer was washed with water and brine (2×30 mL), dried over MgSO4, filtered and concentrated. Purification of the crude material by silica gel chromatography (30-100% EtOAc in hexanes) afforded 3-(6-(azidomethyl)pyridazin-3-yl)-4-fluoro-N,N-dimethylbenzamide (341 mg, 1.14 mmol, 71.0% yield) as a clear colorless film. MS (ESI, pos. ion) m/z: 301.1 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.29 (1 H, dd, J=7.3, 2.1 Hz), 8.02 (1 H, dd, J=8.8, 1.6 Hz), 7.57-7.69 (2 H, m), 7.22-7.31 (1 H, m), 4.81 (2 H, s), 3.08 (3 H, s), 3.13 (3 H, s). 19F NMR (376 MHz, CDCl3) δ ppm −115.30 (1F, s).

Provenance & Evidence