3-Bromo-6-mercaptopyridine

Lawesson's reagent (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 2.32 g, 5.74 mmol) was added in portions to a suspension of 5-bromo-2(1H)-pyridone (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 2 g, 11.5 mmol) in dry toluene (50 mL) under nitrogen. The reaction mixture was heated at reflux for 1 h and then cooled to room temperature. The product that precipitated on cooling was collected by filtration and dried under high vacuum to give 5-bromo-pyridine-2-thiol (2.1 g, 96percent), which was used directly in the next step without further purification.To a solution of Compound 12A (1.92 g, 10 mmol) in DMF (20 mL) was added NaHS (560 mg, 10.0 mmol). The reaction mixture was stirred at 70 C under nitrogen for 14 hours. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3). The combined extracts were washed with brine (100 mL x 2), dried over anhydrous sodium sulfate, filtered, and concentrated to give Compound 12B. LC-MS (ESI) m/z: 190 [M+H]+.

Molecular Weight:190.06
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:188.92478
Monoisotopic Mass:188.92478
Topological Polar Surface Area:44.1
Heavy Atom Count:8
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes