1-((S)-1-tert-butyldiMethylsilyloxyMethyl-2-Methylpropyl)-6-(3-chloro-2-fluorobenzyl)-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 1-((S)-1-tert-butyldiMethylsilyloxyMethyl-2-Methylpropyl)-6-(3-chloro-2-fluorobenzyl)-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• CAS No.: 697762-66-6
• Molecular Formula: C30H38ClF2NO4Si
• Molecular Weight: 578.171
• Mol file: 697762-66-6.mol

Synonyms:

Chemical Property of 1-((S)-1-tert-butyldiMethylsilyloxyMethyl-2-Methylpropyl)-6-(3-chloro-2-fluorobenzyl)-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

Chemical Property:

• PSA: 57.53000
• LogP: 7.91950

Purity/Quality:

98% HPLC ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((S)-1-tert-butyldiMethylsilyloxyMethyl-2-Methylpropyl)-6-(3-chloro-2-fluorobenzyl)-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

There total 11 articles about 1-((S)-1-tert-butyldiMethylsilyloxyMethyl-2-Methylpropyl)-6-(3-chloro-2-fluorobenzyl)-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 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: 83.0%

3-chloro-2-fluorobenzyl zinc bromide (869893-91-4) + 1-((2S)-1-tert-butyldimethylsilyloxy-3-methylbutan-2-yl)-7-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (870294-02-3) → 6-(3-chloro-2-fluorobenzyl)-7-fluoro-1-[1-(S)-tert-butyldimethylsilyloxymethyl-2-methylprop-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (697762-66-6)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 60 ℃; for 1.5h; Product distribution / selectivity;

Reference yield:

ethyl 2-(2,4-difluoro-5-iodobenzoyl)-3-(dimethylamino)acrylate (697762-39-3) → 6-(3-chloro-2-fluorobenzyl)-7-fluoro-1-[1-(S)-tert-butyldimethylsilyloxymethyl-2-methylprop-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (697762-66-6)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran

2: K₂CO₃ / dimethylformamide / 70 °C

3: imidazole / dimethylformamide

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

With 1H-imidazole; trifuran-2-yl-phosphane; potassium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; 4: Negishi coupling;

DOI:10.1021/jm0600139

Reference yield:

7-fluoro-1-(1(S)-hydroxymethyl-2-methylprop-1-yl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (697762-60-0) → 6-(3-chloro-2-fluorobenzyl)-7-fluoro-1-[1-(S)-tert-butyldimethylsilyloxymethyl-2-methylprop-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (697762-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

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

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

DOI:10.1021/jm0600139

upstream raw materials:

3-chloro-2-fluorobenzyl zinc bromide

1-((2S)-1-tert-butyldimethylsilyloxy-3-methylbutan-2-yl)-7-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

ethyl 2-(2,4-difluoro-5-iodobenzoyl)-3-(dimethylamino)acrylate

7-fluoro-1-(1(S)-hydroxymethyl-2-methylprop-1-yl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

Downstream raw materials:

1(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

6-(3-chloro-2-fluorobenzyl)-7-fluoro-1-[2-methyl-1-(tetrahydropyran-2-yloxymethyl)prop-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

1-(S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-methylprop-1-yl]-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

6-(3-chloro-2-fluorobenzyl)-7-methoxy-1-[1-(S)-2-methyl-1-(tetrahydropyran-2-yloxymethyl)prop-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid