N-bromobutanimide → 6-(Bromomethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine

Participants

Reaction Steps

6-Methyl-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine (2.9 g, 10.7 mmol), N-bromosuccinimide (NBS, 1.91 g, 10.7 mmol), CCl4 (200 mL) and benzoyl peroxide (0.021 g) were combined in a three-neck flask (500 mL) under argon. The resulting yellow mixture was stirred at reflux (2 h). Additional NBS (1.91 g) and benzoyl peroxide (0.021 g) were added. After an additional 2 h at reflux, NBS (0.95 g) and benzoyl peroxide (0.021 g) were again added and the mixture was refluxed for 3 h. The mixture was allowed to cool to room temperature and concentrated in vacuo to afford crude 6-(bromomethyl)-2-(2-nitrophenyl)thiazolo[5,4-b]pyridine (4.0 g), which was taken directly to the next step.

Provenance & Evidence