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2-[(3-fluorophenyl)amino]isonicotinonitrile synthesis
- Product Name:2-[(3-fluorophenyl)amino]isonicotinonitrile
- CAS Number:137225-10-6
- Molecular formula:C12H8FN3
- Molecular Weight:213.21
Yield:137225-10-6 75%
Reaction Conditions:
with palladium diacetate;caesium carbonate;2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl in 1,4-dioxane at 80; for 4 h;Sealed tube;Inert atmosphere;Buchwald-Hartwig Coupling;
Steps:
3j 2-((3-fluorophenyl)amino)isonicotinonitrile
General procedure: General Procedure: An oven-dried test tube equippedwith a magnetic stir bar was charged with 2-chloroisonicotinonitrile (69 mg,0.5 mmol), Pd(OAc)2 (2.25 mg, 2 mol%), BINAP (9.38 mg, 3 mol%) , theamine if solid (1.0 mmol), and Cs2CO3 (228 mg, 1.0 mmol).The vessel was then sealed, evacuated, and backfilled with argon (this sequencewas carried out a total of three times). 1,4-dioxane (2.0 mL) and the amine ifliquid (1.0 mmol) via syringe was added successively under an argon atmosphere., and the solution was heated up to 80°C for 4 h in an oil bath. The reactionmixture was allowed to cool to r.t. diluted with dichloromethane, and washed once each withwater and brine, dried over Mg2SO4, filtered, andconcentrated in vacuo. The crude product was then purified by silicagelchromatography mixture of pentane and Et2O or mixture of pentane andethyl acetate. The products were characterized by 1H NMR, 13CNMR and LC-MS.
References:
Guo, Shuo;Wang, Yaping;Sun, Chunxia;Li, Jingya;Zou, Dapeng;Wu, Yangjie;Wu, Yusheng [Tetrahedron Letters,2013,vol. 54,# 25,p. 3233 - 3237] Location in patent:supporting information