3-Quinolinecarboxylic acid, 6-[(3-chloro-2-fluorophenyl)methyl]-1,4-dihydro-1-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-4-oxo-

Base Information

• Chemical Name: 3-Quinolinecarboxylic acid, 6-[(3-chloro-2-fluorophenyl)methyl]-1,4-dihydro-1-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-4-oxo-
• CAS No.: 882534-99-8
• Molecular Formula: C₂₂H₂₁ClFNO₄
• Molecular Weight: 417.864
• Mol file: 882534-99-8.mol

Synonyms:GKPAWDQEYZGYEO-LJQANCHMSA-N;3-Quinolinecarboxylic acid, 6-[(3-chloro-2-fluorophenyl)Methyl]-1,4-dihydro-1-[(1S)-1-(hydroxyMethyl)-2-Methylpropyl]-4-oxo-

Chemical Property of 3-Quinolinecarboxylic acid, 6-[(3-chloro-2-fluorophenyl)methyl]-1,4-dihydro-1-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-4-oxo-

Chemical Property:

• PSA: 79.53000
• LogP: 4.27240

Purity/Quality:

99% ^*data from raw suppliers

6-[(3-CHLORO-2-FLUOROPHENYL)METHYL]-1,4-DIHYDRO-1-[(1S)-1-(HYDROXYMETHYL)-2-METHYLPROPYL]-4-OXO-3-QUINOLINE CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Quinolinecarboxylic acid, 6-[(3-chloro-2-fluorophenyl)methyl]-1,4-dihydro-1-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-4-oxo-

There total 11 articles about 3-Quinolinecarboxylic acid, 6-[(3-chloro-2-fluorophenyl)methyl]-1,4-dihydro-1-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-4-oxo- 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: 74.0%

1-((2S)-1-tert-buthyldimethylsilyloxy-3-methylbutan-2-yl)-6-(3-chloro-2-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (882535-05-9) → (S)-6-(3-Chloro-2-fluorobenzyl)-1-(1-hydroxymethyl-2-methylpropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (882534-99-8)

Guidance literature:

1-((2S)-1-tert-buthyldimethylsilyloxy-3-methylbutan-2-yl)-6-(3-chloro-2-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester; With ethanol; water; sodium hydroxide; for 1h; Reflux;

With acetic acid; at 20 ℃;

DOI:10.1021/jm900460z

Reference yield:

2-fluoro-5-iodobenzoyl chloride (186584-73-6) → (S)-6-(3-Chloro-2-fluorobenzyl)-1-(1-hydroxymethyl-2-methylpropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (882534-99-8)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / 50 °C

2: tetrahydrofuran

3: K₂CO₃ / dimethylformamide / 70 °C

4: imidazole / dimethylformamide

5: Pd(dba)2; trifurylphosphine / tetrahydrofuran / Heating

6: aq. NaOH / ethanol / Heating

With 1H-imidazole; sodium hydroxide; trifuran-2-yl-phosphane; potassium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 5: Negishi coupling;

DOI:10.1021/jm0600139

Reference yield:

3-chloro-2-fluorobenzyl zinc bromide (869893-91-4) → (S)-6-(3-Chloro-2-fluorobenzyl)-1-(1-hydroxymethyl-2-methylpropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (882534-99-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Pd(dba)2; trifurylphosphine / tetrahydrofuran / Heating

2: aq. NaOH / ethanol / Heating

With sodium hydroxide; trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; ethanol; 1: Negishi coupling;

DOI:10.1021/jm0600139

upstream raw materials:

1-((2S)-1-tert-buthyldimethylsilyloxy-3-methylbutan-2-yl)-6-(3-chloro-2-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

2-fluoro-5-iodobenzoyl chloride

3-chloro-2-fluorobenzyl zinc bromide

ethyl 3-(dimethylamino)-2-[(2-fluoro-5-iodophenyl)carbonyl]-2-propenoate