ChemicalBook CAS DataBase List tert-butyl 5-bromo-3-hydroxypyridin-2-ylcarbamate

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

4synthesis methods

Product Name:tert-butyl 5-bromo-3-hydroxypyridin-2-ylcarbamate
CAS Number:1207175-73-2
Molecular formula:C10H13BrN2O3
Molecular Weight:289.13

24424-99-5 Synthesis

24424-99-5
825 suppliers
$13.50/25G

39903-01-0
220 suppliers
$15.00/1g

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

1207175-73-2
72 suppliers
$13.00/100mg

Yield: 98%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 18 h;

Steps:

1 Example 1 The preparation of 5-bromo-3-hydroxy-2-tert-butyloxycarbonylamino pyridine
Example 1 The preparation of 5-bromo-3-hydroxy-2-tert-butyloxycarbonylamino pyridine (0038) To a solution of 2-amino-3-hydroxy-5-bromopyridine (10.0 g, 53.0 mmol) and Et₃N (10 mL, 71.8 mmol) in dichloromethane (100 mL) was added Boc₂O (12.7 g, 58.4 mmol). The mixture was stirred at room temperature for 18 h and continued to stir for 30 min after the addition of 150 ml water. The reaction mixture was filtrated off through celite. The organic layer was separated and the aqueous layer was extracted with 150 dichloromethane. The combined organic layers were washed with saturated NaCl aqueous solution (2×100 mL) and then dried over anhydrous Na₂SO₄. The solvent was removed under reduced pressure and the obtained residue was triturated in hexane (100 mL), filtrated, and dried under vacuum to afford 15.0 g 5-bromo-3-hydroxy-2-tert-butyloxycarbonylamino pyridine as a white solid, with a yield of 98.0%. (0039) ¹H NMR (400 MHz, CDCl₃): δ 7.98 (d, J=2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 4.67 (brs, 2H), 1.56 (s, 9H); ¹C NMR (100 MHz, CDCl₃): δ 150.4, 150.1, 145.3, 133.5, 131.5, 106.5, 85.0, 27.6.

References:

ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTD.;LI, Yuanqiang;QIAN, Jianqiang;CHE, Daqing US2015/307476, 2015, A1 Location in patent:Paragraph 0038-0039

16867-03-1 Synthesis