5-bromo-1H-indazole → 1H-Indazole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

5-Bromo-1H-indazole (Fluorochem; 500 mg; 2.54 mmol), S-Phos (93.8 mg; 0.229 mmol), Pd2(dba)3 (93.0 mg; 0.102 mmol) and zinc cyanide (337.0 mg; 2.87 mmol) were suspended in degassed water:DMF (1:99, 11.5 mL) in a microwave vial and further degassed for 10 minutes in a sonicator. The vial was then sealed and heated in the microwave at 150° C. for 45 minutes. The solid material was removed by filtration and the crude material purified by flash chromatography on a Biotage 40+M column, eluting with DCM containing increasing amounts of methanol. The residue was recrystallised from chloroform/petrol to yield the title compound as an off white solid (1.33 g; 91%). 1H NMR (CDCl3, 400 MHz) δ 10.46 (1 H, br s), 8.20 (2 H, d, J=8.3 Hz), 7.61 (2 H, s).

Provenance & Evidence