7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

Base Information

• Chemical Name: 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide
• CAS No.: 1432728-49-8
• Molecular Formula: C₂₁H₁₆FN₃O₃
• Molecular Weight: 377.375
• Mol file: 1432728-49-8.mol

Synonyms:7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

Chemical Property of 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

There total 8 articles about 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-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: 41.0%

7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carbonitrile (1432731-21-9) → 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432728-49-8)

Guidance literature:

With sodium percarbonate; In water; acetone; at 50 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2020.127066

Reference yield:

7-methylquinoline N-oxide (4053-43-4) → 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432728-49-8)

Guidance literature:

Multi-step reaction with 7 steps

1: N,N-Dimethylcarbamoyl chloride / dichloromethane / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 - 40 °C

3: trichlorophosphate / chloroform / 70 °C

4: N-Bromosuccinimide; dibenzoyl peroxide / acetonitrile / 16 h / 20 °C

5: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 100 °C / Microwave irradiation

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / water; 1,4-dioxane / 4 h / 100 °C

7: sodium percarbonate / water; acetone / 1.5 h / 50 °C

With sodium percarbonate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; trichlorophosphate; dibenzoyl peroxide; In 1,4-dioxane; dichloromethane; chloroform; water; acetone; acetonitrile; 6: |Suzuki Coupling;

Reference yield:

4-chloro-7-methylquinoline-2-carbonitrile (1044278-42-3) → 7-[(2,5-dioxopyrrolidin-1-yl)methyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432728-49-8)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide; dibenzoyl peroxide / acetonitrile / 16 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 100 °C / Microwave irradiation

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / water; 1,4-dioxane / 4 h / 100 °C

4: sodium percarbonate / water; acetone / 1.5 h / 50 °C

With sodium percarbonate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; dibenzoyl peroxide; In 1,4-dioxane; water; acetone; acetonitrile; 3: |Suzuki Coupling;

upstream raw materials:

4-chloro-7-methylquinoline-2-carbonitrile

7-methylquinoline

7-(bromomethyl)-4-chloroquinoline-2-carbonitrile

4-chloro-7-[(2,5-dioxopyrrolidin-1-yl)methyl]quinoline-2-carbonitrile