Nitromethane → HCID 118045789, compound

Temperature

-78 °C

Nitromethane (1.0 mL, 17.20 mmol) was dissolved in THF (34.4 mL), then BuLi (2.5 M in hexanes) (7.22 mL, 18.06 mmol) was added at −78° C. The reaction mixture was stirred at −78° C. for 10 min, then warmed up to room temperature for 20 min. After cooling down to −78° C., (S,E)-N-(3-bromo-5-fluorobenzylidene)-2-methylpropane-2-sulfinamide (4.74 g, 15.48 mmol) in THF (6 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 20 min, warmed up to room temperature, and stirred at room temperature for 5 h. The reaction mixture was quenched by sat NH4Cl, and extracted by EtOAc. The organic was dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (0-40%-100% EtOAC/heptane). Pure fractions were combined to yield (S)—N—((S)-1-(3-bromo-5-fluorophenyl)-2-nitroethyl)-2-methylpropane-2-sulfinamide (2.2 g, 5.99 mmol, 38.7% yield). LCMS (m/z): 367.1/369.1 (MH+), 0.89 min; 1H NMR (400 MHz, CDCl3) δ ppm 7.31 (s, 1H), 7.03 (d, J=9.0 Hz, 1H), 5.03 (q, J=5.7 Hz, 1H), 4.87-4.78 (m, 2H), 4.48 (d, J=5.1 Hz, 1H), 1.33-1.25 (m, 9H).

1. temperaturewarmed up to room temperature for 20 min
2. temperatureAfter cooling down to −78° C.
3. stirringThe reaction mixture was stirred at −78° C. for 20 min
4. temperaturewarmed up to room temperature
5. stirringstirred at room temperature for 5 h
6. customThe reaction mixture was quenched
7. extractionextracted by EtOAc
8. dry with materialThe organic was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude product was purified by flash chromatography (0-40%-100% EtOAC/heptane)

ORD record

ord-00d5f618c47c43108dbc2f8120191ebd

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242996B2