Cesium carbonate → HCID 57633764, compound

Temperature

85 °C

To a solution of a 6:1 mixture of 4-[(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile and 4-[bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.100 g) in acetonitrile (3 mL) was added Cs2CO3 (0.169 g, 0.52 mmol) and methyl bromoacetate (0.080 g, 0.52 mmol). The mixture was heated at 85° C. for 2 h. Upon cooling, additional methyl bromoacetate (0.080 g, 0.52 mmol) was added and heated at 85° C. for 8 h. Upon cooling, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by radial chromatography (10-80% EtOAc-hexanes gradient) to give 0.052 g (50% yield) of the desired product as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.62 (d, J=8.9 Hz, 1H), 6.92 (d, J=2.7 Hz, 1H), 6.76 (dd, J=8.9, 2.7 Hz, 1H), 4.68 (dt, J=47.0, 4.8 Hz, 2H), 4.21 (s, 2H), 3.81 (dt, J=25.6, 4.8 Hz, 2H), 3.78 (s, 3H).

1. temperatureUpon cooling
2. temperatureheated at 85° C. for 8 h
3. temperatureUpon cooling
4. customthe mixture was partitioned between ethyl acetate and water
5. washThe organic phase was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by radial chromatography (10-80% EtOAc-hexanes gradient)

ORD record

ord-b305b2ed108f44cf850114bfcbf651f0

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514470B2