ChemicalBook CAS DataBase List tert-butyl 4-(tert-butoxycarbonylamino)-2,6-dichloronicotinate

tert-butyl 4-(tert-butoxycarbonylamino)-2,6-dichloronicotinate synthesis

5synthesis methods

Product Name:tert-butyl 4-(tert-butoxycarbonylamino)-2,6-dichloronicotinate
CAS Number:1044148-92-6
Molecular formula:C15H20Cl2N2O4
Molecular Weight:363.24

1044148-88-0 Synthesis

tert-butyl 4-((tert-butoxycarbonyl)amino)-2,6-dichloronicotinate

1044148-88-0
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1044148-92-6
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Yield:1044148-92-6 100%

Reaction Conditions:

with lithium diisopropyl amide in tetrahydrofuran at -78; for 0.5 h;Inert atmosphere;

Steps:

2 Step 2-Tert-butyl 4-(tert-butoxycarbonylamino)-2,6-dichloro-pyridine-3-carboxylate

To a solution of LDA (2 M, 169 mL) was added a solution of tert-butyl N-tert-butoxycarbonyl-N-(2,6-dichloro-4-pyridyl)carbamate (35.0 g, 96.4 mmol) in THF (600 mL) under nitrogen at -78° C. The reaction mixture was stirred at -78° C. for 0.5 hr. On completion, the reaction mixture was quenched with saturated NH₄Cl, and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE:EA=200:1) to give the title compound (35.0 g, 100% yield) as a white solid. ¹H NMR (400 MHz, CDCl₃) δ 8.99 (s, 1H), 8.35 (s, 1H), 1.64 (s, 9H), 1.54 (s, 9H).

References:

US2019/192668,2019,A1 Location in patent:Paragraph 2642; 2644