(S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

Base Information

Chemical Name:(S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide
CAS No.:1310737-17-7
Molecular Formula:C₂₉H₂₇BrN₂O₅S₂
Molecular Weight:627.58
Hs Code.:

Synonyms:(S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

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Chemical Property of (S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

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Technology Process of (S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

There total 5 articles about (S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide 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: 83.0%

: 1273005-86-9
(S)-N-[2-(hydroxymethyl)but-3-ynyl]-4-methylbenzenesulfonamide

: 1310737-15-5
(Z)-4-bromo-3-(2-bromovinyl)-1-tosyl-1H-indole

: 1310737-17-7
(S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo2008324

Reference yield:

: 1310737-16-6
4-bromo-3-(2,2-dibromovinyl)-1-tosyl-1H-indole

: 1310737-17-7
(S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride / toluene / 8.5 h / 20 °C / Inert atmosphere

2: copper(l) iodide; dichloro bis(acetonitrile) palladium(II); diisopropylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; diisopropylamine; In tetrahydrofuran; toluene; 2: Sonogashira coupling;
DOI:10.1021/jo2008324

Reference yield:

: 181271-32-9
4-bromo-1-(4-toluenesulfonyl)indole-3-carboxaldehyde

: 1310737-17-7
(S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine / dichloromethane / 0.25 h / -20 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride / toluene / 8.5 h / 20 °C / Inert atmosphere

3.1: copper(l) iodide; dichloro bis(acetonitrile) palladium(II); diisopropylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 3.1: Sonogashira coupling;
DOI:10.1021/jo2008324