Pyridine, 3-bromo-2-ethoxy-5-methyl- (9CI) synthesis

Yield:760207-82-7 72%

Reaction Conditions:

in ethanol at 100; for 48 h;Inert atmosphere;

Steps:

Intermediate 6 3-Bromo-2-ethoxy-5-methylpyridine

3-Bromo-2-ethoxy-5-methylpyridine
To a solution of 3-bromo-2-chloro-5-methylpyridine (4.00 g, 19.37 mmol) in ethanol (100 mL) was added sodium ethoxide (6.59 g, 96.9 mmol) in three portions.
The mixture was stirred under nitrogen at 100° C. for 2 days.
The reaction was cooled to room temperature, diluted with water and extracted with DCM.
The combined organic layers were dried (Na₂SO₄), and the solvent was removed under reduced pressure.
Purification (FCC, SiO₂, 20%, EtOAc/hexanes) afforded the title compound (3.00 g, 72%).
¹H NMR (400 MHz, DMSO-d₆) δ 7.94 (dd, J=0.8, 2.3 Hz, 1H), 7.89-7.82 (m, 1H), 4.31 (q, J=7.0 Hz, 2H), 2.18 (t, J=0.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

References:

US2014/275531,2014,A1 Location in patent:Paragraph 0365; 0366