ChemicalBook CAS DataBase List 2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole synthesis

4synthesis methods

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 Synthesis

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2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

73590-60-0
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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): t_R = 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

86604-78-6 Synthesis

3,5-Dimethyl-4-methoxy-2-pyridinemethanol

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References

2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine

84006-10-0
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$38.00/250mg

73590-60-0
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References

84006-10-0
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134469-07-1
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73590-60-0
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References

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