trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid

Base Information

• Chemical Name: trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid
• CAS No.: 1309956-55-5
• Molecular Formula: C₂₆H₂₂N₂O₂S
• Molecular Weight: 426.539

Synonyms:trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid

Chemical Property of trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid

Chemical Property:

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Technology Process of trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid

There total 3 articles about trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid 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: 78.0%

5-(4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophene-2-carbaldehyde (1309956-58-8) + cyanoacetic acid (372-09-8) → trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid (1309956-55-5)

Guidance literature:

With piperidine; In acetonitrile; for 6h; Reflux; Inert atmosphere;

DOI:10.1039/c1cp20484j

Reference yield:

(5-formylthiophen-2-yl)boronic acid → trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid (1309956-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran / 24 h / Reflux; Inert atmosphere

2: piperidine / acetonitrile / 6 h / Reflux; Inert atmosphere

With piperidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In tetrahydrofuran; acetonitrile;

DOI:10.1039/c1cp20484j

Reference yield:

7-bromo-1,2,3,3a,4,8b-hexahydro-4-(4-methylphenyl)-cyclopent-[b]indole (1250863-85-4) → trans-2-cyano-3-(5-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophen-2-yl)acrylic acid (1309956-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran / 24 h / Reflux; Inert atmosphere

2: piperidine / acetonitrile / 6 h / Reflux; Inert atmosphere

With piperidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In tetrahydrofuran; acetonitrile;

DOI:10.1039/c1cp20484j

upstream raw materials:

7-bromo-1,2,3,3a,4,8b-hexahydro-4-(4-methylphenyl)-cyclopent-[b]indole

5-(4-(p-tolyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)thiophene-2-carbaldehyde

cyanoacetic acid

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