ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate

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Chemical Name:ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate
CAS No.:1339939-29-5
Molecular Formula:C₂₄H₂₅BrN₂O₆S
Molecular Weight:549.442
Hs Code.:

Synonyms:ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate

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Chemical Property of ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate

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Technology Process of ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate

There total 6 articles about ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

: ethyl (E/Z)-3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-2-nitroacrylate

: 38614-36-7
2-methylpropen-1-ylmagnesium bromide

: 1339939-29-5
ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate

Guidance literature:: 2-methylpropen-1-ylmagnesium bromide; With zinc(II) chloride; In tetrahydrofuran; toluene; at 0 ℃; for 0.25h; Inert atmosphere;

ethyl (E/Z)-3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-2-nitroacrylate; In tetrahydrofuran; toluene; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tet.2011.08.094

Reference yield:

: 52488-36-5
4-bromo-1H-indole

: 1339939-29-5
ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine; trichlorophosphate / 0.75 h / 35 °C / Inert atmosphere; Cooling with ice

1.2: 0.03 h / 100 °C / Inert atmosphere; Cooling with ice

2.1: dmap; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: titanium tetrachloride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: zinc(II) chloride / tetrahydrofuran; toluene / 0.25 h / 0 °C / Inert atmosphere

4.2: 2 h / 0 °C / Inert atmosphere

With pyridine; dmap; titanium tetrachloride; triethylamine; zinc(II) chloride; trichlorophosphate; In tetrahydrofuran; dichloromethane; toluene; 1.1: Vilsmeier formylation / 3.1: Henry reaction / 4.2: Michael condensation;
DOI:10.1016/j.tet.2011.08.094

Reference yield:

: 1280538-41-1
C₁₂H₁₃BrN₂O₂

: 1339939-29-5
ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: iron; acetic acid / ethanol / 0.5 h / 50 °C / Reflux; Inert atmosphere

2.1: pyridine; trichlorophosphate / 0.75 h / 35 °C / Inert atmosphere; Cooling with ice

2.2: 0.03 h / 100 °C / Inert atmosphere; Cooling with ice

3.1: dmap; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

4.1: titanium tetrachloride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

5.1: zinc(II) chloride / tetrahydrofuran; toluene / 0.25 h / 0 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

With pyridine; dmap; titanium tetrachloride; iron; acetic acid; triethylamine; zinc(II) chloride; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; toluene; 2.1: Vilsmeier formylation / 4.1: Henry reaction / 5.2: Michael condensation;
DOI:10.1016/j.tet.2011.08.094