Iodine → HCID 87103646, compound

Participants

Reaction Steps

To a solution of 0.988 mL 2,2,6,6-tetramethylpiperidine in 10 mL tetrahydrofuran was added 3.534 mL of a 1.6M solution of n-butyl lithium in hexane at ambient temperature and the mixture was stirred at room temperature for 30 min. To this solution was added rapidly a pre-cooled (−75° C.) solution of 0.300 g 3-chloro-6-cyclopropylmethoxy-pyridazine in 10 mL tetrahydrofuran at −75° C. After 5 minutes, a precooled solution of 0.701 g iodine in 10 mL THF was added rapidly. The reaction mixture was stirred at −75° C. for 30 minutes and then quenched with a saturated aqueous solution of ammonium chloride and diluted with ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate=95:5 to 50:50 to yield 0.206 g of the title compound as light yellow solid, MS 310.9 (M+H)+.

Provenance & Evidence