Réaction #9478

Équation de réaction

(5-bromopyridin-3-yl)methanol

Iodoethane

DMF

Sodium bis(trimethylsilyl)amide

→

(5-Bromopyridin-3-yl)methanol

3-bromo-5-ethoxymethylpyridine

Rendement 120.4%

Solvants

THF

THF

Brine

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred overnight
2. 2
   Extractionthe aqueous layer was extracted twice with hexanes
3. 3
   ConcentrationThe combined organic fractions were concentrated under reduced pressure
4. 4
   Autrethe residue was purified by HPFC (
5. 5
   Lavageeluting with hexanes

Mode opératoire

(5-Bromopyridin-3-yl)methanol was prepared according to the published procedure (Zhang, N. et al, J. Med. Chem., 45, 2832–2840 (2002)). A solution of (5-bromopyridin-3-yl)methanol (7.39 g, 39.3 mmol) in THF was cooled to 0° C. Sodium bis(trimethylsilyl)amide (39.3 mL of a 1.0 M solution in THF) was added, and the reaction was stirred for 20 minutes. Iodoethane (3.46 mL, 43.2 mmol) and DMF were added, and the reaction was allowed to warm to ambient temperature and stirred overnight. Brine was added, and the aqueous layer was extracted twice with hexanes. The combined organic fractions were concentrated under reduced pressure, and the residue was purified by HPFC (eluting with hexanes:ethyl acetate in a gradient from 100:0 to 70:30) to provide 5.11 g of 3-bromo-5-ethoxymethylpyridine as a colorless oil.

Source