Water → 2,2-Difluoro-2-(2-pyridyl)ethylazide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5.5 g of 2,2-difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate 6-4 in 70 mL of DMF was added 6.74 g (104 mmol) of sodium azide under Ar. The mixture was heated to 60° C. overnight. A second batch was run in the same manner, and after cooling to rt, both reactions were poured into 600 mL of water, and extracted with 3×500 mL of ether. The combined extracts were washed with brine, dried over Na2SO4 and concentrated at reduced pressure to give an oil that was purified by SiO2 (10×6 cm) using hexane 1:3 EtOAc-hexane and 1:1 EtOAc-hexane. The product-containing fractions were concentrated at reduced pressure to give 6-5 as a yellow oil: 1H NMR (CDCl3) δ 4.05 (t, 2H), 7.4-7.45 (m, 1H), 7.73 (d, 1H), 7.83-7.89 (m, 1H), 8.67 (d, 1H).

Provenance & Evidence