ChemicalBook CAS DataBase List CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester

CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester synthesis

5synthesis methods

Product Name:CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester
CAS Number:1220910-89-3
Molecular formula:C21H17FN6O2
Molecular Weight:404.4

N-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]carbamic Acid Phenylmethyl Ester is an intermediate in the synthesis of Tedizolid (T013750), an known oral and intravenous antibiotic. It can be prepared by suzuki reaction of 2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine and Benzyl (4- broMo-3-fluorophenyl)carbaMate.

2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine

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510729-01-8 Synthesis

Benzyl (4-broMo-3-fluorophenyl)carbaMate

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CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester

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Yield: 88%

Reaction Conditions:

with potassium carbonate in water at 80; for 12 h;Inert atmosphere;

Steps:

2 Example 2:synthesis of 3-fluoro-4 - (6 - (2-methyl -2H-tetrazole-5-yl) pyridin-3-yl) phenyl-carbamic acid benzyl ester (compound 1)
Compound 2 (120g, 0.5mol), potassium acetate (145g, 0.5mol) and frequencymellow joint boron is (150g, 0.6mol) 10L in four-mouth bottle, by adding 1,4-dioxane (3L) and Pd (dppf)₂Cl₂·CH₂Cl₂(20g, 25mmol). After the protection of nitrogen, heating to 80 °C, reaction 3 hours. Combined liquid detection for determining compound 2 is fully converted to compound 3 the rear, the compound is added 4 (146g, 0.45mol), potassium carbonate (173g, 1.2mol) and water (1L), re-protection of nitrogen, heating to 80 °C reaction 12 hours. LCMS determining the reaction is complete. Filtering, filtering the solid material, the filtrate obtained by reducing pressure and evaporating the evaporimeter 1,4-dioxane, is added to the aqueous phase 500 ml ethanol, beating sleepovers. Filtering, the filter cake is washed with cold-b activity, reduced-pressure drying 4 hours. The crude product in ethyl acetate, heating reflow, holding 5 minutes, the heat filters. Then reducing the temperature to room temperature, the beating sleepovers, filtering, washing the filter cake by ethyl acetate, to obtain compound 1 (177g, 88%), yellow solid.

References:

Cai Ping;Cai, Ping;Chen, Jing CN105367547, 2016, A Location in patent:Paragraph 0034; 0035; 0036