ChemicalBook CAS DataBase List t-butyl 6-bromo-3-pyridinecarboxylate

t-butyl 6-bromo-3-pyridinecarboxylate synthesis

4synthesis methods

Product Name:t-butyl 6-bromo-3-pyridinecarboxylate
CAS Number:941294-58-2
Molecular formula:C10H12BrNO2
Molecular Weight:258.11

6311-35-9 Synthesis

6311-35-9
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$15.00/1g

36805-97-7 Synthesis

N,N-Dimethylformamide di-tert-butyl acetal

36805-97-7
155 suppliers
$29.00/1g

941294-58-2
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$45.00/50mg

Yield: 52%

Reaction Conditions:

in toluene for 72 h;Heating / reflux;

Steps:

3.1
To a solution of the 6-bromonicotinic acid (2.5 g, 12.4 mmol) in toluene (25 ml_) was added dimethylformamide di-te/f-butylacetal (5.0 g, 24.8 mmol). The solution was then heated to relfux overnight. Additional dimethylformamide di- terf-butylacetal (10.0 g, 59.6 mmol) was added in two portions over 24 h with continued stirring at reflux. The solution was stirred at reflux for a total of 72 h then cooled to RT. To the solution was added sat. NaHCO₃ (aq.) and the aqueous layer was extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over Na₂SO₄, filtered and concentrated. The crude product was purified via flash chromatography (SiO₂: gradient elution, 100:0 to 92:8 hexanes: EtOAc) to afford the ester (1.68 g, 52%).

References:

SCHERING CORPORATION WO2009/5671, 2009, A2 Location in patent:Page/Page column 125-126

6311-35-9 Synthesis

6311-35-9
372 suppliers
$15.00/1g

865-47-4 Synthesis