methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

Base Information

Chemical Name:methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate
CAS No.:1269632-16-7
Molecular Formula:C₂₇H₂₂N₂O₆S
Molecular Weight:502.547
Hs Code.:

Synonyms:methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

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Chemical Property of methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

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Technology Process of methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

There total 9 articles about methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-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: 80.0%

: 1269632-15-6
diethyl {3-[1-(methoxycarbonyl)prop-1-en-2-yl]-1-(phenylsulfonyl)-indol-2-yl}methylphosphonate

: 552-89-6
2-nitro-benzaldehyde

: 1269632-16-7
methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

Guidance literature:: diethyl {3-[1-(methoxycarbonyl)prop-1-en-2-yl]-1-(phenylsulfonyl)-indol-2-yl}methylphosphonate; With sodium hydride; In tetrahydrofuran; at -10 ℃; for 0.25h; Inert atmosphere;

2-nitro-benzaldehyde; In tetrahydrofuran; at -10 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol200094b

Reference yield:

: 1269632-14-5
methyl 3-[2-bromomethyl-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

: 1269632-16-7
methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2 h / Reflux; Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere

2.2: 2 h / -10 °C / Inert atmosphere

With sodium hydride; In tetrahydrofuran; 1.1: Michaelis-Arbuzov reaction / 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol200094b

Reference yield:

: 95-20-5
2-methyl-1H-indole

: 1269632-16-7
methyl (2E)-3-[2-(2-nitrostyryl)-1-(phenylsulfonyl)indol-3-yl]but-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: iron(III) chloride / 1,2-dichloro-ethane / 3 h / Inert atmosphere

2.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 2 h / 20 °C / Inert atmosphere

3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Reflux; Inert atmosphere

4.1: 2 h / Reflux; Inert atmosphere

5.1: sodium hydride / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere

5.2: 2 h / -10 °C / Inert atmosphere

With iron(III) chloride; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; sodium hydroxide; In tetrahydrofuran; tetrachloromethane; water; 1,2-dichloro-ethane; toluene; 4.1: Michaelis-Arbuzov reaction / 5.1: Horner-Wadsworth-Emmons olefination / 5.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol200094b