Iodine → N-(3-Iodopyridin-2-yl)-2,2-dimethylpropanamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,2-dimethyl-N-pyridin-2-yl-propionamide described in Preparation Example 1-1-1 (3.0 g, 17 mmol), N,N,N′,N′-tetramethyl ethylenediamine (6.3 mL, 42 mmol) and tetrahydrofuran (60 mL) was added n-butyl lithium (1.6M n-hexane solution, 30 mL, 47 mmol) dropwise at −78° C, which was stirred overnight at 0° C. To the reaction mixture was added iodine (6.8 g, 27 mmol) at −78° C, which was stirred at 0° C for 1.5 hours. To the reaction mixture were added water and a saturated aqueous solution of sodium thiosulfate, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride water, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the title compound (2.9 g).

Provenance & Evidence