4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide

Base Information

• Chemical Name: 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide
• CAS No.: 1231883-83-2
• Molecular Formula: C₃₂H₂₉FN₆O₃
• Molecular Weight: 564.619

Synonyms:4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide

Chemical Property of 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide

There total 9 articles about 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide 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: 92.0%

5-fluoropicolinic acid (107504-08-5) + 4-(3-amino-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (1231881-82-5) → 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (1231883-83-2)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 18h;

Reference yield:

5-bromo-2-(ethoxycarbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid → 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (1231883-83-2)

Guidance literature:

Multi-step reaction with 6 steps

1: benzotriazol-1-ol; 1,2-dichloro-ethane; ammonium hydroxide / dichloromethane; tetrahydrofuran / 20 °C / Inert atmosphere

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3: lithium hydroxide monohydrate / ethanol; water; tetrahydrofuran / 6 h / Reflux; Inert atmosphere

4: benzotriazol-1-ol; 1,2-dichloro-ethane / dichloromethane; tetrahydrofuran; N,N-dimethyl-formamide / 20 °C / Inert atmosphere

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 11 h / 90 °C / Inert atmosphere

6: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole / acetonitrile / 18 h / 20 °C / Inert atmosphere

With ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; sodium carbonate; benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.6b00722

Reference yield:

2-amino-4-bromobenzoic acid (20776-50-5) → 4-(3-(5-fluoropicolinamido)-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (1231883-83-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium nitrite; hydrogenchloride / water / 0.17 h / -5 °C / Inert atmosphere

1.2: 1 h / -5 - 20 °C / Inert atmosphere

2.1: acetic acid / 2.5 h / Reflux; Inert atmosphere

3.1: benzotriazol-1-ol; 1,2-dichloro-ethane; ammonium hydroxide / dichloromethane; tetrahydrofuran / 20 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / ethanol; water; tetrahydrofuran / 6 h / Reflux; Inert atmosphere

6.1: benzotriazol-1-ol; 1,2-dichloro-ethane / dichloromethane; tetrahydrofuran; N,N-dimethyl-formamide / 20 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 11 h / 90 °C / Inert atmosphere

8.1: 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole / acetonitrile / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; sodium carbonate; benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: |Fischer Indole Synthesis / 7.1: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.6b00722

upstream raw materials:

5-fluoropicolinic acid

4-(3-amino-2-methylphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide

2-amino-4-bromobenzoic acid

ethyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate

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