ChemicalBook CAS DataBase List 2-Bromo-6-methoxy-4-pyridinecarboxylic acid methyl ester

2-Bromo-6-methoxy-4-pyridinecarboxylic acid methyl ester synthesis

7synthesis methods

Product Name:2-Bromo-6-methoxy-4-pyridinecarboxylic acid methyl ester
CAS Number:853030-09-8
Molecular formula:C8H8BrNO3
Molecular Weight:246.06

124-41-4 Synthesis

124-41-4
724 suppliers
$12.00/25g

Methyl 2,6-dibromopyridine-4-carboxylate

119308-57-5
96 suppliers
$40.00/1g

2-Bromo-6-methoxy-4-pyridinecarboxylic acid methyl ester

853030-09-8
36 suppliers
inquiry

Yield: 44%

Reaction Conditions:

in 2-methyltetrahydrofuran at 60; for 0.966667 h;Reflux;Large scale;

Steps:

1.1
The solution of methyl 2,6-dibromoisonicotinate (4.84 kg, KF=0.03% w/w) is placed in a 20 L reactor and the reaction medium is then heated to 60° C. A solution of NaOMe at 25% w/w in MeTHF (0.73 kg, 6.5 mol, 1 eq.) is introduced over 58 minutes [Ti=59.3° C.→m.p.=65.5° C.]. A sample is taken for HPLC analysis: 87.5% of methyl 2-bromo-6-methoxyisonicotinate. The reaction medium is cooled to 30° C. and then washed successively with saturated NaHCO₃solution (8.0 L) and then again with saturated NaHCO₃solution (2.0 L) and finally with saturated NaCl solution (3.0 L). The organic phase is distilled off and the residue (m=0.90 kg) is then taken up in isopropanol (5.0 L), heated to reflux and cooled to 20° C. (start of crystallization observed at 45° C.) and then to 0° C. The solid is filtered off and rinsed with isopropanol (1.2 L). The solid is dried in a vacuum oven at 45° C. to constant mass. Production of 691 g of methyl 2-bromo-6-methoxyisonicotinate. Yield=44%. HPLC purity=>99.0%. (0217) 1H NMR (400 MHz, CDCl₃): 7.58 (s, 1H); 7.26 (s, 1H); 3.96 (s, 3H), 3.93 (s, 3H).

References:

Galderma Research & Development;BOITEAU, Jean-Guy;DAVER, Sébastien;RODEVILLE, Nicolas US2019/10124, 2019, A1 Location in patent:Paragraph 0212; 0216; 0217

124-41-4 Synthesis

124-41-4
724 suppliers
$12.00/25g

119308-57-5
96 suppliers
$40.00/1g

853030-09-8
36 suppliers
inquiry

52606-00-5 Synthesis