Sodium hydride → 5-Bromo-2-(cyclopropylthio)pyridine

To a suspension of NaH (60% in mineral oil, 2.40 g) in THF (100 mL) was added dropwise cyclopropanethiol (0.25 M in Et2O, 160 mL) at 0° C. After stirring for 30 min, 5-bromo-2-fluoropyridine (3.52 g) was added in portions at 0° C. and then warmed to r.t. slowly. The reaction mixture was stirred at r.t. overnight. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine (50 mL) and dried over Na2SO4. After filtration and evaporation of the solvent, the crude product was obtained and used in next step without further purification.

1. stirringThe reaction mixture was stirred at r.t. overnight
2. customThe reaction mixture was quenched with water (30 mL)
3. extractionextracted with ethyl acetate (50 mL×3)
4. washThe combined organic layers were washed with brine (50 mL)
5. dry with materialdried over Na2SO4
6. filtrationAfter filtration and evaporation of the solvent

ORD-Eintrag

ord-d37b9c32ba424f93a83b57ad25cdabb5

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853412B2