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

Temperature

0 °C

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).

1. stirringwhich was stirred at 0° C for 1.5 hours
2. extractiona saturated aqueous solution of sodium thiosulfate, and extracted with ethyl acetate
3. washThe organic layer was washed with saturated sodium chloride water
4. customthe solvent thereof was evaporated under a reduced pressure
5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=2:1)

ORD record

ord-7795249d65e64efaa4e87de6bccb07e4

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058444B2