Yield:138428-37-2 100%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in dichloromethane at 0 - 20; for 3 h;

Steps:

General procedure for the syntheses of 2-(pyridin-2-yl)ethyl methanesulfonate (10) and 2-(pyridazin-3-yl)ethylmethanesulfonate (11)

General procedure: To the opportune alcohol (2 mmol) in dichloromethane(5 mL), DIPEA (4 mmol) was added and the solution wascooled at 0 °C. Subsequently methanesulfonyl chloride(2.2 mmol) was added and the mixture was stirred at roomtemperature for 3 h. Afterwards water (5 mL) was addedand the organic layer was separated, washed with a solutionof NaHCO3(5 mL), dried and concentrated under vacuum.The obtained yellow oils were used in the next step withoutfurther purification.Intermediate 10. Yield: quantitative; 1H NMR (300 MHz,CDCl3)δ 2.95 (s, 3H), 3.42 (t, J = 6 Hz, 2H), 4.75 (t,J = 6 Hz, 2H), 7.39-7.48 (m, 2H), 9.08-9.14 (m, 1H);

References:

Villa, Stefania;Legnani, Laura;Colombo, Diego;Gelain, Arianna;Lammi, Carmen;Bongiorno, Daniele;Ilboudo, Denise P.;McGee, Kellen E.;Bosch, Jürgen;Grazioso, Giovanni [Journal of Computer-Aided Molecular Design,2018,vol. 32,# 3,p. 473 - 486]