methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate

Base Information

Chemical Name:methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate
CAS No.:1414703-83-5
Molecular Formula:C₄₁H₅₅N₃O₈SSi
Molecular Weight:778.054
Hs Code.:

Synonyms:methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate

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Chemical Property of methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate

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Technology Process of methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate

There total 3 articles about methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-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:

: 1414703-82-4
methyl 2-bromo-3-[4-nitro-1-(phenylsulfonyl)-1H-indol-3-yl]prop-2-enoate

: 1414703-83-5
methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: iron; ammonium chloride / isopropyl alcohol; water / 2 h / 60 °C

2: dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere

3: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 70 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron; potassium carbonate; ammonium chloride; In 1,4-dioxane; dichloromethane; water; isopropyl alcohol; 3: |Suzuki Coupling;
DOI:10.1016/j.ejmech.2012.08.029

Reference yield:

: 1414703-85-7
methyl 3-[4-amino-1-(phenylsulfonyl)-1H-indol-3-yl]-2-bromoprop-2-enoate

: 1414703-83-5
methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere

2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 70 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; dichloromethane; water; 2: |Suzuki Coupling;
DOI:10.1016/j.ejmech.2012.08.029

Reference yield:

: 1414703-81-3
4-nitro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde

: 1414703-83-5
methyl 3-{4-[bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)-1H-indol-3-yl}-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]prop-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / dichloromethane / 0.75 h / -20 °C / Inert atmosphere

1.2: 48 h / -20 - 20 °C

2.1: iron; ammonium chloride / isopropyl alcohol; water / 2 h / 60 °C

3.1: dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere

4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 70 °C / Inert atmosphere

With dmap; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron; potassium carbonate; ammonium chloride; In 1,4-dioxane; dichloromethane; water; isopropyl alcohol; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 4.1: |Suzuki Coupling;
DOI:10.1016/j.ejmech.2012.08.029