Dimethyl Sulfoxide → HCID 71150652, compound

Participants

Reaction Steps

To a solution of (E)-methyl 3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-4-(((methylsulfonyl)oxy)imino)-1,4,5,6-tetrahydropyridine-2-carboxylate (200 mg, 0.44 mmol) in DMSO (1.4 mL) was added K2CO3 (181 mg, 1.3 mmol) followed by sodium thiomethoxide (93 mg, 1.3 mmol). After 10 min the reaction was quenched with 1 M HCl solution and then extracted with diethyl ether. The organics were washed with brine, dried with Na2SO4, filtered and purified by silica gel chromatography eluting with 30% Et2O in pentane to yielded to afford a brown solid (56 mg, 34%): mp 93-94° C.; 1H NMR (300 MHz, CDCl3) δ 7.67 (dd, J=8.6, 7.7 Hz, 1H), 7.22 (m, 1H), 7.11 (d, J=1.9 Hz, 1H), 5.16 (s, 2H), 4.47 (q, J=7.1 Hz, 2H), 3.96 (d, J=0.9 Hz, 3H), 2.30 (d, J=1.7 Hz, 3H), 1.43 (t, J=7.1 Hz, 3H); ESIMS m/z 369 ([M−H]−).

Provenance & Evidence