1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

Base Information

Chemical Name:1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester
CAS No.:1171823-27-0
Molecular Formula:C₃₀H₄₀ClFN₂O₅Si
Molecular Weight:591.195
Hs Code.:

1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

Synonyms:1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

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Chemical Property of 1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

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Technology Process of 1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

There total 2 articles about 1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-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:

: 503000-87-1
2-chloro-6-methoxypyridine-3-carboxylic acid

: 1171823-27-0
1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: bromine / acetic acid

2: thionyl chloride; N,N-dimethyl-formamide / toluene

3: triethylamine / tetrahydrofuran

4: tetrahydrofuran

5: potassium carbonate / N,N-dimethyl-formamide

6: 1H-imidazole / N,N-dimethyl-formamide

7: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; thionyl chloride; bromine; potassium carbonate; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; toluene; 7: Negishi coupling reaction;
DOI:10.1016/j.bmcl.2010.11.108

Reference yield:

: 869893-91-4
3-chloro-2-fluorobenzyl zinc bromide

: 1171823-26-9
6-bromo-1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

: 1171823-27-0
1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

Guidance literature:: bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 60 ℃; for 1.5h; Inert atmosphere;

Reference yield: 79.0%

: 1171823-27-0
1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

: 1171821-04-7
6-(3-chloro-2-fluoro-benzyl)-1-((S)-1-hydroxymethyl-2-methyl-propyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

Guidance literature:: 1-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-6-(3-chloro-2-fluoro-benzyl)-7-methoxy-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester; With sodium methylate; In methanol; for 4h; Reflux;

With hydrogenchloride; In water;