Sodium Carbonate → HCID 66712636, compound

Participants

Reaction Steps

A suspension of N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (0.29 g, 0.93 mmol), 1-bromo-2-methyl-4-nitrobenzene (0.20 g, 0.93 mmol), PdCl2(PPh3)2 (0.03 g, 0.05 mmol) and 3 M aqueous Na2CO3 (0.93 mL, 2.8 mmol) in 1,4-dioxane (10 mL) was degassed with nitrogen for 10 minutes then heated at reflux for 16 hours. The resulting mixture was concentrated under reduced pressure and purified using silica gel column chromatography (Biotage Isolera, SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.) to give the title compound A38 (0.25 g, 83%); 1H NMR (400 MHz, CDCl3) δ 8.05 (d, J=2.4 Hz, 1H), 8.03-7.98 (m, 1H), 7.22 (d, J=8.4 Hz, 1H), 5.63 (s, 1H), 4.09-4.04 (m, 2H), 3.64 (t, J=5.6 Hz, 2H), 2.38 (s, 3H), 2.35 (s, 2H), 1.51 (s, 9H).

Provenance & Evidence