Ethyl Acetate → N-(5-bromo-2-methoxypyridin-3-yl)acetamide

A suspension of 5-bromo-2-methoxy-3-nitro-pyridine (Stage 63.1.4, 450 mg, 1.93 mmol) and tin dichloride (1.465 mg, 7.72 mmol) in EtOAc (30 ml) was refluxed for 3 h. The reaction mixture was evaporated to dryness and then quenched with cold 3 M aqueous NaOH (50 ml) and CH2Cl2 (50 ml) and stirred for 3 h at rt. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with 30 ml sat. aqueous NaHCO3, dried over Na2SO4, filtered and evaporated. The crude product was dry loaded on silica gel and purified by MPLC (CH2Cl2/MeOH 0% to 4%) to give after evaporation the title compound as an off-white solid (HPLC: tR 2.72 min (Method A); M+H=245, 247 MS-ES).

1. temperaturewas refluxed for 3 h
2. customThe reaction mixture was evaporated to dryness
3. customquenched with cold 3 M aqueous NaOH (50 ml) and CH2Cl2 (50 ml)
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with CH2Cl2
6. washThe combined organic layers were washed with 30 ml sat. aqueous NaHCO3
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customevaporated
10. dry with materialThe crude product was dry
11. custompurified by MPLC (CH2Cl2/MeOH 0% to 4%)
12. customto give
13. customafter evaporation the title compound as an off-white solid (HPLC: tR 2.72 min (Method A); M+H=245, 247 MS-ES)

ORD record

ord-8f7a54513bbd4014869d8dd4697850f3

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2