5-(TRIFLUOROMETHYL)NICOTINONITRILE synthesis
- Product Name:5-(TRIFLUOROMETHYL)NICOTINONITRILE
- CAS Number:951624-83-2
- Molecular formula:C7H3F3N2
- Molecular Weight:172.11
557-21-1
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436799-33-6
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951624-83-2
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Yield: 44%
Reaction Conditions:
Stage #1:dicyanozinc;3-bromo-5-(trifluoromethyl)pyridine;tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide at 80;
Stage #2: with ammonia in diethyl ether;water;N,N-dimethyl-formamide at 20;
Steps:
1.1.27
Example 1.1.27: (5-(trifluoromethyl)pyridin-3-yl)methanamine; 3-bromo-5-(trifluoromethyl)pyridine (1.0 g, 4.42 mmol, 1 eq) was dissolved in 20 mL anhydrous DMF. The solution was degassed by bubbling through with Ar. Zn(CN)2 (0.312 g, 2.65 mmol, 0.6 eq) and Pd(PPh3)4 were added, and the resulting solution was heated to 80 0C with stirring overnight. The reaction was cooled to room temperature and diluted with Et2O. NH4OH (28%) was added with stirring and the layers were separated. The organic layer was washed with water (x3), brine (xl), and dried over Na2SO4. The inorganics were filtered off, and the reaction mixture was concentrated in vacuo. Purification via flash chromatography on silica gel yielded 0.310 g (1.95 mmol, 44% yield) of 5- (trifluoromethyl)nicotinonitrile.
References:
COMENTIS, INC.;PURDUE RESEARCH FOUNDATION WO2009/42694, 2009, A1 Location in patent:Page/Page column 84
35590-37-5
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81290-20-2
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951624-83-2
49 suppliers
$58.60/250mg