Iodine → HCID 178477831, compound

Participants

Reaction Steps

A solution of 6-chloro-5-[4-(morpholin-4-yl)phenyl]-1H-indazole (72 mg, 0.23 mmol) and N,N-dimethylformamide (3 mL) was treated with iodine (91 mg, 0.36 mmol) and freshly ground potassium hydroxide (16 mg, 0.26 mmol). The reaction mixture was stirred at room temperature for three hours, then treated with additional iodine (50 mg) and potassium hydroxide (20 mg) and heated to 40° C. for 20 minutes. The reaction mixture was poured into ethyl acetate and saturated aqueous ammonium chloride. The layers were separated and the organic phase was washed with 2N sodium thiosulfate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography utilizing heptanes/ethyl acetate (100:0 to 0:70) to give the title compound (86.7 mg). MS (ES−): 438.0 (M−H)−.

Provenance & Evidence