Methyl iodide → 2-(4-(4-Fluorophenyl)thiazol-2-yl)propanenitrile

Temperature

-78 °C

To a stirred solution of 2-(4-(4-fluorophenyl)thiazol-2-yl)acetonitrile (500 mg, 2.29 mmol) in THF (10 mL) at −78° C. was added LiHMDS (1M in THF; 2.06 mL, 2.06 mmol) and the reaction mixture was stirred at −78° C. for 10 min. Iodomethane (0.12 mL, 2.06 mmol) in THF (2 mL) was then added dropwise and the reaction mixture was stirred at −78° C. for 30 min. The reaction mixture was diluted with EtOAc, washed with saturated aqueous NH4Cl solution, water, brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to give the crude product; which was purified on a Teledyne ISCO automated column chromatography system (0-30% EtOAc/Hexanes) to give 2-(4-(4-fluorophenyl)thiazol-2-yl)propanenitrile (180 mg, yield 34%). MS (ESI) m/z: Calculated for C12H9FN2S: 232.05. found: 233.1 (M+H)

1. stirringthe reaction mixture was stirred at −78° C. for 30 min
2. washwashed with saturated aqueous NH4Cl solution, water, brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationThe organic layer was concentrated under reduced pressure
5. customto give the crude product
6. customwhich was purified on a Teledyne ISCO automated column chromatography system (0-30% EtOAc/Hexanes)

ORD record

ord-65035f3ac9904c0b9e50999c8b80ea80

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901156B2