N-bromobutanimide → Ethyl 4-amino-3-bromo-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

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Reaction Steps

To a stirred solution of ethyl 4-amino-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (6.44 g, 25.7 mmol) (Description 5) in DCM (110 mL), was added N-bromosuccinimide (9.16 g, 51.5 mmol) and the resulting mixture was stirred for 1 h. The mixture was concentrated and the solid that precipitated was filtered and washed with DCM (3×10 mL), to afford the title compound (9.44 g). LCMS (A) m/z: 329/331 [M+1]+, Rt 1.22 min (acidic).

Provenance & Evidence