ChemicalBook CAS DataBase List ethyl 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate

ethyl 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate synthesis

6synthesis methods

Product Name:ethyl 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate
CAS Number:308831-94-9
Molecular formula:C24H22F2N2O6S
Molecular Weight:504.5

308831-93-8 Synthesis

ethyl 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate

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85118-00-9 Synthesis

85118-00-9
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ethyl 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate

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Yield:308831-94-9 88.6%

Reaction Conditions:

with potassium carbonate;potassium iodide in N,N-dimethyl-formamide at 25; for 16 h;

Steps:

4.1.2. ethyl 2-((2,6-difluorobenzyl) (ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl) thiophene-3-carboxylate (6a)

KI (51.91 g, 312.71 mmol, 1.1 eq) and K2CO3 (43.22 g, 312.71 mmol,1.1 eq) were added to a solution of compound 5 (107.57 g, 284.28mmol, 1 eq) in DMF (3400 mL) A solution of 2,6-Difluorobenzyl bromide(55.46 g, 341.14 mmol, 1.2 eq) in DMF (200 mL) was then added to themixture. The mixture was then stirred at 25 C for 16 h. LCMS showedthat the starting material was consumed completely and one peak withdesired MS was detected. The mixture was poured into water (700 mL)and extracted with EtOAc (300 mL × 2). The combined organic layerwas washed with water (500 mL), brine (500 mL), dried over anhydrousNa2SO4, and concentrated under reduced pressure. The residue wassuspended in 600 ml of methyl-tert-butyl ether, and stirred at 25 C for30 min. After filtration, the filter cake was washed by 100 mL of methyltert-butyl ether and dried under vacuum to afford 6a (127 g, 251.73mmol, 88.6 yield) as a yellow solid. MS m/z (ESI): 505[M+H]+. 1H NMR(400 MHz, CDCl3) 1.20 (s, 2H), 1.33 (t, J = 6.80 Hz, 4H), 2.40 (s, 3H),4.18-4.34 (m, 4H), 4.98 (s, 2H), 6.86 (t, J = 8.00 Hz, 2H), 7.22-7.31 (m,1H), 7.52 (d, J = 8.80 Hz, 2H), 8.25-8.30 (m, 2H).

References:

Zou, Fangxia;Wang, Yao;Yu, Dawei;Liu, Chunjiao;Lu, Jing;Zhao, Min;Ma, Mingxu;Wang, Wenyan;Jiang, Wanglin;Gao, Yonglin;Zhang, Rui;Zhang, Jianzhao;Ye, Liang;Tian, Jingwei [European Journal of Medicinal Chemistry,2022,vol. 242,art. no. 114679]

308831-93-8 Synthesis

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697-73-4 Synthesis