4-Bromo-2-chlorobenzothiazole

Pale yellow solid

In a 500 mL round-bottom flask equipped with a temperature probe were added NaHMDS (88 mL, 87.8 mmol) and THF (98 mL) under nitrogen. The solution was cooled at -60 C. MeCN (3.1 mL, 58.5 mmol) was added dropwise and the mixture was stirred at the same temperature for 40 mm. A solution of 4-bromo-2-chlorobenzo[djthiazole (7.27 g, 29.3 mmol) in THF (88 mL) was then cannulated to the reaction flask over 15 mm and the resulting mixture was stirred at 0 C for 40 mm. A saturated aqueous solution of NH4C1 (400 mL) and water (400 mL) were added. The resulting mixture was extracted with EtOAc (2 x 250 mL) and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. Trituration of the crude material with EtOAc (2 x 10 mL) afforded the title compound (7.37 g, 100%) as a brown solid.In a 1000 mL round-bottom flask under nitrogen were added DMF (7.9 mL, 101.6 mmol) and DCE (300 mL). Oxalyl chloride (8.6 mL, 101.6 mmol) was added dropwise at 0 C and the white suspension was allowed to stir at 20 C for 30 mi 4, 6-Dimethylthiazolo[4, 5-cjpyridine-2(3H)- thione (10.0 g, 40.6 mmol) was then added directly to the reaction mixture and the flask was mounted with a condenser. The suspension was heated in a 85 C oil bath for 1.5 h and it was allowed to cool down at 20 C. A saturated aqueous solution of NaHCO3 (400 mL) and water (100 mL) were added. The resulting mixture was extracted with DCM (2 x 100 mL) and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. In order to get completion, the crude mixture was resubmitted to reaction conditions using DMF (2.4 mL, 30.5 mmol) and oxalyl chloride (2.6 mL, 30.5 mmol) in DCE (30 mL). The crude product obtained after work-up was purified on a Si02 pad (EtOAc and DCM in hexane, 4:1:95 gradient) to afford the title compound (8.27 g, 82%) as a beige solid.

Molecular Weight:248.53
XLogP3:4
Hydrogen Bond Acceptor Count:2
Exact Mass:246.88581
Monoisotopic Mass:246.88581
Topological Polar Surface Area:41.1
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes