Tesmilifene Hydrochloride → 5-Bromo-2-nitrothiophene-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-nitrothiophene-3-carbaldehyde oxime (45 g, 179 mmol), p-toluenesulfonic acid monohydrate (2.73 g, 14.34 mmol), dppe (1.428 g, 3.58 mmol) and Ru(PPh3)3(CO)H2 (3.29 g, 3.58 mmol) were taken up in toluene (750 mL). The flask was evacuated and back-filled with N2 (3×) before stirring at 111° C. under N2 for 24 hours. After cooling to room temperature, the reaction mixture was purified directly by flash silica gel column chromatography (0-100% EtOAc/toluene) to give the title compound as brown needles after recrystallising from EtOH-hexanes.

Provenance & Evidence