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tert-butyl 6-bromo-5-fluoropyridin-2-ylcarbamate synthesis

2synthesis methods
-

Yield:1446793-48-1 99%

Reaction Conditions:

with diphenyl phosphoryl azide;triethylamine in tert-butyl alcohol at 25 - 70; for 2.33333 h;

Steps:

34.1 Step 1

Into a 250 mL round-bottom flask, was placed 6-bromo-5-fluoropyridine-2- carboxylic acid (6.3 g, 28.6 mmol, 1 eq), t-BuOH (50 mL), TEA (4 mL, 28.8 mmol, 1 eq), DPPA (6.2 mL, 23 mmol, 0.79 eq). The resulting solution was stirred for 20 min at 25°C then refluxed for 2 h at 70°C in an oil bath. The resulting solution was diluted with water, extracted with 3x350 mL of ethyl acetate, and concentrated. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether. This resulted in 8.67 g (99%) of tert-butyl N-(6-bromo-5- fluoropyridin-2-yl)carbamate as yellow oil. LCMS: m/z = 291.1 [M+H]+.

References:

WO2019/241131,2019,A1 Location in patent:Paragraph 00402