N,N,N',N'-Tetramethylethylenediamine → HCID 58641590, compound

Temperature

-78 °C

A mixture of 5-bromo-2-fluoropyridine (2.05 g, 11.7 mmol) and N1,N1,N2,N2-tetramethylethane-1,2-diamine (2.27 mL, 15.1 mmol) was purged with nitrogen for 45 minutes. Toluene (116 mL) was added and the reaction mixture was cooled to −78° C. N-butyllithium (2.5 M in hexanes, 5.59 mL, 14.0 mmol) was added dropwise over 6 minutes. The reaction mixture was stirred at −78° C. for 1 hour. Dimethyl disulfide (1.26 mL, 14.0 mmol) was added. The reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was warmed to 0° C., then immediately quenched with saturated aqueous ammonium chloride. The layers were separated, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate/heptane) to provide the title compound (1.00 g, 60%).

1. customwas purged with nitrogen for 45 minutes
2. additionToluene (116 mL) was added
3. stirringThe reaction mixture was stirred at −78° C. for 1 hour
4. temperatureThe reaction mixture was warmed to 0° C.
5. customimmediately quenched with saturated aqueous ammonium chloride
6. customThe layers were separated
7. washthe organic layer was washed with saturated aqueous sodium chloride
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography (10% ethyl acetate/heptane)

ORD record

ord-a0aea54dad31492684807f38f03e701d

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296741B2