Methyl iodide → HCID 13541933, compound

Temperature

-78 °C

To the cooled (-78° C.) solution of TMEDA (516.5 mg, 4.40 mmol) in anhydrous THF (10 mL) was slowly added sec-butyl lithium (1.3 M, 3.38 mL, 4.40 mmol), and the resultant solution was stirred at -78° C. for 10 minutes. 3-Pyridyl diethylcarbamate (776 mg, 4.0 mmol) in THF (3 mL) was slowly added, and the mixture was stirred at -78° C. for 30 minutes. Iodomethane (275.4 μL, 4.40 mmol) was then added, and the mixture was stirred for two hours. Brine (1 mL) was added, and the mixture was slowly warmed up to room temperature. The organic layer was decanted, and the residue washed with ethyl acetate (3×5 mL). The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by chromatography on silica gel eluting with hexane/EtOAc (1:2 and 0:1) to provide 765 mg (92% yield) of the title compound. TLC Rf 0.28 (1:2 hexane/EtOAc). MS (DCI/NH3) m/e 209 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.34 (s, 1H, ArH), 8.32 (d, J=6.9 Hz, 1H, ArH), 7.16 (d, J=69 Hz, 1H, ArH), 3.48 (q, J=7.5 Hz, 2H, NCH2), 3.41 (q, J=7.5 Hz, 2H, NCH2), 1.28 (t, J=7.5 Hz, 3H, CH3), 1.22 (t, J=7.5 Hz, 3H, CH3).

1. stirringthe mixture was stirred for two hours
2. temperaturethe mixture was slowly warmed up to room temperature
3. customThe organic layer was decanted
4. washthe residue washed with ethyl acetate (3×5 mL)
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated
7. customThe crude product was purified by chromatography on silica gel eluting with hexane/EtOAc (1:2 and 0:1)

ORD record

ord-45aeb9689d2f486eb29fda8b62948b19

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05914328