Methyl iodide → HCID 59578436, Verbindung

Temperatur

-78 °C

To a solution of DIPA (1.71 mL, 12 mmol) in THF (50 mL) at −78° C. was added 1.6M BuLi (7.5 mL, 12.0 mmol) and the mixture was stirred at −78° C. for 2 h. The LDA solution was cannulated into a solution of 3-bromo-4-chloropyridine (2.117 g, 11 mmol) in THF (50 mL) at −78° C., and the mixture was stirred at −78° C. for 1 h. A solution of N-(cyclopropylmethylene)methanesulfonamide (10 mmol, crude mixture) in THF (50 mL) was added and the mixture was stirred at −78° C. for 1 h. A solution of MeI (0.625 mL, 10 mmol) in THF (10 mL) was added, and the mixture was warmed to room temperature and stirred overnight. Water (0.5 mL) was added and the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a 0-50% EtOAc-heptane gradient to give N-((5-bromo-4-chloropyridin-3-yl)(cyclopropyl)methyl)-N-methylmethanesulfonamide. MS (ESI): m/z 353.0, 355.0 (M+H)+.

1. stirringthe mixture was stirred at −78° C. for 1 h
2. stirringthe mixture was stirred at −78° C. for 1 h
3. temperaturethe mixture was warmed to room temperature
4. stirringstirred overnight
5. concentrationthe mixture was concentrated in vacuo
6. customThe residue was purified by silica gel chromatography
7. washeluting with a 0-50% EtOAc-heptane gradient

ORD-Eintrag

ord-4d2480c9553a40798ecae9f1c0e51ad7

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08383827B2