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

Participants

Reaction Steps

To a solution of 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (500 mg, 1.51 mmol), from Synthetic Preparation 6, in THF (10 mL) at 0° C. was added lithium aluminum hydride (61 mg, 1.66 mmol). After 30 min, the reaction was quenched by the slow addition of EtOAc followed by 0.4N NaHSO4, and extracted. The organic layer was washed with brine, dried, and concentrated. The crude product was purified by flash chromatography to give 5-iodo-1H-indazole-3-carboxaldehyde (240 mg, 58.2%).

Provenance & Evidence