2-Bromopyridine → HCID 67957992, compound

Temperature

-100 °C

To a solution of 2-bromopyridine (0.16 g, 1.02 mmol, 1.0 eq) in dry THF at −100° C. was slowly added a solution of n-BuLi in hexane (2.5M, 0.41 ml, 1.03 mmol, 1 eq), and reaction mixture was then kept in same temperature for 30 minute. A mixture of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (0.18 g, 1.02 mmol, 1 eq) and a 2M solution of Me3Al (0.5 ml, 1 mmol, 1 eq) in toluene was stirred at −78° C. for 10 minutes, and then added to the above reaction mixture slowly. The reaction temperature was maintained at −100° C. for another 1 h, after which the reaction mixture warmed to 0° C. slowly. The reaction mixture was quenched with a saturated solution of Na2SO4 and extracted with ethyl acetate. The organic layer was separated and washed with a saturated brine solution, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified through a neutral alumina column using 0.5% MeOH/DCM. Yield: 0.1 g (38.5%).

1. additionadded to the above reaction mixture slowly
2. temperatureafter which the reaction mixture warmed to 0° C. slowly
3. customThe reaction mixture was quenched with a saturated solution of Na2SO4
4. extractionextracted with ethyl acetate
5. customThe organic layer was separated
6. washwashed with a saturated brine solution
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationthe filtrate concentrated
10. customThe crude product was purified through a neutral alumina column

ORD record

ord-82b3b1b3345c4a168dd8364fe106455b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507683B2