Iodine → HCID 87103646, compound

To a solution of 0.988 ml 2,2,6,6-tetramethylpiperidine in 10 ml tetrahydrofurane 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 precooled (−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 (EI): 310.9 (M+H).

1. waitAfter 5 minutes
2. stirringThe reaction mixture was stirred at −75° C. for 30 minutes
3. customquenched with a saturated aqueous solution of ammonium chloride
4. additiondiluted with ethyl acetate
5. customThe phases were separated
6. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

ORD record

ord-cdd1f7b7093243c1acff1f5937f778ca

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08669254B2