ChemicalBook CAS DataBase List 1-Piperidinecarboxylic acid, 4-[[[4-(2-fluoro-4-nitrophenoxy)-6-methoxy-7-quinolinyl]oxy]methyl]-, 1,1-dimethylethyl ester

1-Piperidinecarboxylic acid, 4-[[[4-(2-fluoro-4-nitrophenoxy)-6-methoxy-7-quinolinyl]oxy]methyl]-, 1,1-dimethylethyl ester synthesis

9synthesis methods

Product Name:1-Piperidinecarboxylic acid, 4-[[[4-(2-fluoro-4-nitrophenoxy)-6-methoxy-7-quinolinyl]oxy]methyl]-, 1,1-dimethylethyl ester
CAS Number:849217-45-4
Molecular formula:C27H30FN3O7
Molecular Weight:527.54

4-(2-fluoro-4-nitro-phenoxy)-6-Methoxy-quinolin-7-ol

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161975-39-9 Synthesis

1-BOC-4-METHANESULFONYLOXYMETHYL-PIPERIDINE

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1-Piperidinecarboxylic acid, 4-[[[4-(2-fluoro-4-nitrophenoxy)-6-methoxy-7-quinolinyl]oxy]methyl]-, 1,1-dimethylethyl ester

849217-45-4
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Yield:849217-45-4 56%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 80; for 2.5 h;

Steps:

17

[0268] To a solution of the 4-(2-fluoro-4-nitro-phenoxy)-6-methoxy-7-hydroxyquinoline (609 mg, 1.8 mmol) in DMF (9 mL) was added K₂CO₃ (1.24 g, 9.0 mmol) and N-Boc-4- piperidinemethanol mesylate (732 mg, 2.5 mmol). The mixture was then stirred at 80 °C for 2.5 h. After it was cooled to rt, the mixture was loaded directly to a Biotage column, and eluted with solvents (hexanes:EtOAc = 1 :3). The resulting product, 4-[4-(2-fluoro-4- nitro-phenoxy)-6-methoxy-quinolin-7-yloxymethyl]-piperidine-l -carboxylic acid tert- butyl ester, was obtained as a solid (556 mg, 56%).

References:

WO2006/108059,2006,A1 Location in patent:Page/Page column 86