2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid

Base Information

• Chemical Name: 2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid
• CAS No.: 1610430-76-6
• Molecular Formula: C₃₁H₁₉N₅O₂S₂
• Molecular Weight: 557.656

Synonyms:2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid

Chemical Property of 2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid

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Technology Process of 2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid

There total 5 articles about 2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}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: 84.0%

4-{4-[5-(diphenylamino)thiophen-2-yl]-[1,2,5]thiadiazolo[3,4-c]pyridin-7-yl}benzaldehyde (1610430-79-9) + cyanoacetic acid (372-09-8) → 2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid (1610430-76-6)

Guidance literature:

With ammonium acetate; acetic acid; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2014.04.039

Reference yield:

3,4-diamino-2,5-dibromopyridine (221241-11-8) → 2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid (1610430-76-6)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / 16 h / Reflux

2: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 12 h / 95 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium carbonate / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere

4: ammonium acetate; acetic acid / 12 h / Inert atmosphere; Reflux

With bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; ammonium acetate; water; potassium carbonate; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; 2: |Stille Cross Coupling / 3: |Suzuki Coupling / 4: |Knoevenagel Condensation;

DOI:10.1016/j.tet.2014.04.039

Reference yield:

3,4-diaminopyridine (54-96-6) → 2-cyano-3-{4-[4-(5-(diphenylamino)thiophen-2-yl)-[1,2,5]-thiadiazolo[3,4-c]pyridin-7-yl]phenyl}acrylic acid (1610430-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen bromide; water / Reflux

1.2: 16 h / 80 °C

2.1: thionyl chloride / 16 h / Reflux

3.1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 12 h / 95 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; potassium carbonate / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere

5.1: ammonium acetate; acetic acid / 12 h / Inert atmosphere; Reflux

With bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; ammonium acetate; water; hydrogen bromide; potassium carbonate; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; 3.1: |Stille Cross Coupling / 4.1: |Suzuki Coupling / 5.1: |Knoevenagel Condensation;

DOI:10.1016/j.tet.2014.04.039

upstream raw materials:

3,4-diamino-2,5-dibromopyridine

3,4-diaminopyridine

7-bromo-4-chloro-[1,2,5]thiadiazole-[3,4-c]pyridine

5-(7-bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)-N,N-diphenylthiophen-2-amine

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