5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide → 5-formyl-N-methoxy-N-methyl-1H-indazole-3-carboxamide

Participants

Reaction Steps

A mixture of 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (5 g, 15.1 mmol), HCOONa (1.85 g, 30.2 mmol), and PdCl2(PPh3)2 (320 mg, 0.453 mmol) in DMF (20 mL) was put under vacuum, and charged with CO. This process was repeated three times, and the mixture was kept at 110° C. for 6 hr. After cooling to rt, the reaction mixture was diluted with brine and extracted with EtOAc. The organic phases were combined, washed with brine, dried, and concentrated. The crude product was purified by column chromatography to afford 5-formyl-N-methoxy-N-methyl-1H-indazole-3-carboxamide (550 mg, 15.6%) as a white solid.

Provenance & Evidence