반응 #494435

반응 방정식

sodium thiomethoxide

(E)-methyl 3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-4-(((methylsulfonyl)oxy)imino)-1,4,5,6-tetrahydropyridine-2-carboxylate

K2CO3

DMSO

→

solid

수율 34.0%

Ethyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-3-(methylthio)picolinate

수율 34.0%

반응 조건

후처리

1. 1
   기타After 10 min the reaction was quenched with 1 M HCl solution
2. 2
   추출extracted with diethyl ether
3. 3
   세척The organics were washed with brine
4. 4
   건조dried with Na2SO4
5. 5
   여과filtered
6. 6
   기타purified by silica gel chromatography
7. 7
   세척eluting with 30% Et2O in pentane
8. 8
   기타to yielded

실험 절차

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]−).

출처