(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine synthesis

7synthesis methods

Product Name:(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine
CAS Number:1569895-70-0
Molecular formula:C18H18BrCl2FN2O3
Molecular Weight:480.16

877397-65-4 Synthesis

(S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol

877397-65-4
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$17.39/250mg

1207175-73-2 Synthesis

tert-butyl 5-bromo-3-hydroxypyridin-2-ylcarbamate

1207175-73-2
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$13.00/100mg

(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine

1569895-70-0
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Yield:1569895-70-0 94.3%

Reaction Conditions:

with di-isopropyl azodicarboxylate;triphenylphosphine in tetrahydrofuran at 0 - 20; for 6 h;Inert atmosphere;

Steps:

5 The preparation of (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylamino-pyridine

Example 5 The preparation of (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylamino-pyridine (0045) (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol (1.0 g, 4.78 mmol, ee 99.9%), 5-bromo-3-bromo-3-hydroxyl-tert-butyloxycarbonylamino pyridine (1.4 g, 4.78 mmol) and triphenylphosphine (1.6 g, 6.2 mmol) were dissolved in 20 ml of anhydrous THF under N₂atmosphere, cooled to below 0° C. and then diisopropylazodiformate (1.25 g, 6.2 mmol) was added to the mixture at below 5° C. The mixture was stirred at room temperature for 6 h and then filtered. The solvent was evaporated under reduced pressure to afford product as oil which was recrystallized by ethanol to produce 2.16 g of 5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylamino pyridine as a white solid with a yield of 94.3%, ee 99.9%.

References:

US2015/307476,2015,A1 Location in patent:Paragraph 0045