2-bromo-5-(2-methoxyethoxy)pyridine synthesis

Yield:1144110-14-4 42%

Reaction Conditions:

Stage #1: 2-bromo-5-hydroxypyridinewith sodium hydride in N,N-dimethyl-formamide; for 0.5 h;
Stage #2: 2-Bromoethyl methyl ether in N,N-dimethyl-formamide; for 72 h;

Steps:

17.A

2-Bromo-5-hydroxypyridine (1 mmol) is dissolved in DMF (2.5 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min 1-Bromo-2-methoxy-ethane (1.1 eq.) is added and the reaction solution is stirred 3 days. The reaction solution is pored into water and extracted with methyl-tert.-butyl ether. The combined organic layers are dried over MgSO₄ and the solvent is removed in vacuo. 2-Bromo-5-(2-methoxy- ethoxy)-pyridine is obtained after column chromatography as colorless powder in a yield of 42 %; HPLC (method C): 1.48 min; LC-MS (method A): 1.11 min, 231.95 (M+H⁺).

References:

WO2009/46784,2009,A1 Location in patent:Page/Page column 65