Iodine → 6-(5-Iodoisoxazol-3-yl)isoquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(5-(tributylstannyl)isoxazol-3-yl)isoquinoline (1.00 g, 2.1 mmol) in 20 mL of THF in a sealable tube was added iodine (0.52 g, 2.1 mmol). The tube was sealed and heated to 80° C. by immersion in an oil bath. After 12 hours, the mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (0 to 2.5% MeOH/DCM), affording 6-(5-iodoisoxazol-3-yl)isoquinoline (0.60 g, 90% yield) as a grey powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.40 (s, 1H), 8.59 (d, J=5.6 Hz, 1H), 8.52 (s, 1H), 8.27 (d, J=8.6 Hz, 1H), 8.12 (dd, J=1.6 Hz, 8.6 Hz, 1H), 7.92 (d, J=5.7 Hz, 1H).

Provenance & Evidence