Iodine → 4-Chloro-2-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

Temperature

-78 °C

4-Chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (235 mg, 0.831 mmol) was dissolved in tetrahydrofuran (3 mL) under nitrogen atmosphere. After cooling to −78° C., n-butyllithium (0.675 mL, 1.080 mmol, 1.6 M hexane solution) was slowly added dropwise. The resulting mixture was stirred for 1 hour. After adding a solution of iodine (253 mg, 0.997 mmol) in tetrahydrofuran (2 mL), the mixture was slowly heated to room temperature. One hour later, the mixture was extracted with dichloromethane and water and the organic layer was washed with sodium chloride aqueous solution. The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1) to give the target compound as a yellow oil (339 mg, 0.83 mmol, 97% yield).

1. temperaturethe mixture was slowly heated to room temperature
2. extractionOne hour later, the mixture was extracted with dichloromethane and water
3. washthe organic layer was washed with sodium chloride aqueous solution
4. dry with materialThe organic layer was dried with magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1)

ORD record

ord-f3a592e8f7a7472eb039c5ba8a532674

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957102B2