7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

Base Information

• Chemical Name: 7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide
• CAS No.: 1432730-82-9
• Molecular Formula: C₂₃H₁₇ClFN₃O₂
• Molecular Weight: 421.858
• Mol file: 1432730-82-9.mol

Synonyms:7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

Chemical Property of 7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide

There total 9 articles about 7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-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:

7-[2-(6-chloropyridin-3-yl)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432730-84-1) → 7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432730-82-9) + 7-[2-(6-chloropyridin-3-yl)-(1S)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432730-83-0)

Guidance literature:

With Chiralpak AD; In ethanol; hexane; diethylamine; Resolution of racemate;

Reference yield:

7-methylquinoline (612-60-2) → 7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432730-82-9) + 7-[2-(6-chloropyridin-3-yl)-(1S)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432730-83-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 34 °C

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

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

4: trichlorophosphate / chloroform / 70 °C

5: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 16 h / 100 °C

6: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 5 h / Reflux

7: silver nitrate; water / 1,4-dioxane / 24 h / Reflux

8: tetrahydrofuran / 0.33 h / 50 °C

9: Chiralpak AD / ethanol; hexane; diethylamine / Resolution of racemate

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); water; sodium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; ethanol; hexane; dichloromethane; chloroform; water; diethylamine; 5: |Suzuki Coupling;

Reference yield:

7-(dibromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile (1432731-45-7) → 7-[2-(6-chloropyridin-3-yl)-(1R)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432730-82-9) + 7-[2-(6-chloropyridin-3-yl)-(1S)-1-hydroxyethyl]-4-(4-fluorophenyl)quinoline-2-carboxamide (1432730-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1: silver nitrate; water / 1,4-dioxane / 24 h / Reflux

2: tetrahydrofuran / 0.33 h / 50 °C

3: Chiralpak AD / ethanol; hexane; diethylamine / Resolution of racemate

With water; silver nitrate; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; diethylamine;

upstream raw materials:

4-chloro-7-methylquinoline-2-carbonitrile

7-(dibromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile

4-(4-fluorophenyl)-7-formylquinoline-2-carboxamide

4-(4-fluorophenyl)-7-methylquinoline-2-carbonitrile