3-(DIMETHYLAMINO)-2-[3-(TRIFLUOROMETHYL)PHENYL]ACRYLONITRILE synthesis

Yield:62738-99-2 50%

Reaction Conditions:

with N,N,N,N,-tetramethylethylenediamine for 5 h;Reflux;

Steps:

1.54

54. 4-((3-(3-(Trifluoromethyl)Dhenyl)Dyrazoloi1 ,5-alDyrimidin-5-yl)amino) - trans-cvclohexanol EX. 8-54). [00419] A mixture of 2-(3-(trifluoromethyl)phenyl)acetonitrile (4.55 g, 24.58 mmol), 1 ,1 -dimethoxy-N,N-dimethylmethanamine (13.10 ml, 98 mmol), and N¹ ,N¹,N²,//²-tetramethylethane-1 ,2-diamine (0.737 ml, 4.92 mmol) were heated to reflux for 5h. After cooling to RT, the mixture was partitioned between saturated aqueous NH CI and EtOAc and extracted three times with EtOAc. The combined organics were washed with brine, dried over Na₂SO₄, and concentrated in vacuo. After absorbing on celite, the compound was purified by Isco (40g silica, 10% to 70% EtOAc/hexanes) to give pure 3-(dimethylamino)-2- (3-(trifluoromethyl)phenyl)acrylonitrile (2.93g, 50% yield). [00420] ¹ H NMR (400 MHz, CDCIs): 7.48 (m, 2H), 7.41 -7.34 (m, 2H), 6.94 (s, 1 H), 3.25 s, 6H).

References:

WO2013/13188,2013,A1 Location in patent:Paragraph 00419; 00420