2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole synthesis
- Product Name:2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
- CAS Number:73590-60-0
- Molecular formula:C16H17N3O2S
- Molecular Weight:315.39
73590-87-1
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Yield:73590-60-0 66.8%
Reaction Conditions:
with sodium hypochlorite;sodium hydroxide in water;ethyl acetate at 20;
Steps:
General Procedure for the synthesis of 1-4 and 7.
General procedure: To a solution of intermediates 6 (2.01 mmol), or 11b-11e was dissolved in ethyl acetate (20 mL). The mixture was added NaOH solution (0.05 g/mL, 4mL) and aqueous sodium hypochlorite solution (50%, 3mL). After 1 h -4 h stirring at room temperature, the reaction mixture was then quenched with 2M NaOH to pH = 8-9. The solution was extracted several times with DCM, and the combined organic layers were washed saturated salt solution, dried over anhydrous MgSO4 and then evaporated in vacuo. The crude material was purified by normal phase column chromatography (200:1 DCM/MeOH) to afford target compound 1-4 and 7. 2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole (1): : white solid, yield 66.8 %; m.p. >200 °C. 1H NMR (300 MHz, DMSO-d6) δ 8.27 (s, 1H), 7.51-7.47 (m, 2H), 6.92-6.88 (m, 2H), 4.70 (d, J = 13.2 Hz, 1H), 4.44 (d, J = 13.0 Hz, 1H), 3.72 (s, 3H), 2.24 (s, 6H). 13C NMR (75 MHz, DMSO-d6) δ 163.91, 162.48, 152.12, 149.57, 147.09, 126.99, 125.56, 118.94, 117.82, 61.03, 60.23, 13.48, 11.79. HRMS (ESI): calcd. for m/z C16H17N3O2S, [M+H]+ 316.11197, found 316.11157. HPLC (80:20 MeOH/H2O): tR = 9.11 min, 97.1%.
References:
Chen, Wei-Lin;Chen, Xin;Guo, Xiao-Ke;Jiang, Zheng-Yu;Li, Dong-Dong;Wang, Ying-Zhe;Xu, Jun-Jie;You, Qi-Dong [European Journal of Medicinal Chemistry,2020,vol. 188] Location in patent:supporting information
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