2-FLUORONICOTINICACIDMETHYLESTER

General procedure: To a solution of 2, 3-dichloropyridine(1.00 g, 6.76 mmol) in DMSO (33.8 ml) was added CsF (2.053 g, 13.51mmol) at room temperature. The mixture was stirred at 110 °C under air for 20h. The mixture was quenched with water at room temperature and extracted withEtOAc. The organic layer was separated, washed with water and brine, dried overNaPREPARATION 18Methyl 2-fluoropyridine-3-carboxylate; 2 M lithium diisopropyl amide (11.3 mL, 22.5 mmol) is slowly added over a solution of 2-fluoropyridine (2 g, 20.5 mmol) in tetrahydrofuran (90 mL) under nitrogen atmosphere at -78 C. After 4 h at that temperature methyl chloroformate (1.9 mL, 24.6 mmol) is added and the mixture is stirred for an additional hour at -78 C. and allowed to reach room temperature overnight. Reaction mixture is slowly poured over water and extracted in diethyl ether. Organic layer is washed with brine, dried over sodium sulfate and solvent is evaporated in vacuo. Residue is purified by normal phase Isco chromatography eluting with hexane/diethyl ether (9/1) to give 495.2 mg of the title compound. MS (m/z): 156 (M+1).General procedure: A solution of [Ir(COD)OMe]2 (5mol%), dtbpy (5 mol%) and B2pin2 (1.2mol %) in MTBE (0.4M) wasprepared in a sealed vial and an aliquot then added to a thick-walled microwave synthesis vial containing the starting pyridine . The vessel was sealed with a crimp top septum cap and shaken until allof the substrate was dissolved. The reaction mixture was stirred on a magnetic stirring block or irradiated in a microwave reactor for the stated time and temperature. Upon completion, the volatiles were removed in vacuo to afford the crude borylated product. To the crude mixture under N2, was added palladium catalyst (5 mol%), base (2 eq.), aryl halide (1.1 - 2eq.) and the stated solvent. The reaction was heated at the stated temperature for the stated time. The reaction mixture was diluted with water and extracted into EtOAc. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give the crude product. This was dry-loaded onto silica geland purified by silica gel flash column chromatography using the stated solvent system.To a stirred mixture of

Molecular Weight:155.13
XLogP3:1.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:155.03825660
Monoisotopic Mass:155.03825660
Topological Polar Surface Area:39.2
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes