2-FLUOROISONICOTINONITRILE

Preparation 50; 2-Fluoro-isonicotinonitrile; Treat a solution of 2-chloro-4-cyanopyridine (6.0 g, 43.5 mmol) and potassium fluoride (7.56 g, 130.3 mmol) in 1-methyl-2-pyrrolidinone (20 mL) with tetrabutylphosphonium bromide (14.8 g, 43.7 mmol) and heat to 100 °C for 18 hours. Dilute with water and extract with EtOAc. Wash EtOAc with water, brine, dry with Na2S04, and concentrate to give the title compound (2.3 g, 43percent). MS (ES) 123.1 (M+1) +. 'H NMR (400 MHz, CHC13) 6 8.43 (d, 1H, J = 5.2 Hz), 7.45 (m, 1H), 7.22 (m, 1H).Thionyl chloride (2.6 mL) was added slowly to a stirred solution of compound 1002 (4.0 g in 40 mL of THF) at 0 C. After stirring for 1 hour at room temperature, the volatiles were removed in vacuo. The residue was taken up in ethyl acetate (50 mL) and the organics were washed with water and brine. The organics were concentrated in vacuo to give 2-fluoropyridine-4-carbonitrile (compound 1003) as a white solid (3.0 g; ESMS: M+H+=123).General procedure: General Procedure E: General Experimental Details for NMR Yields Reported in Figure 3. In a drybox, anhydrous NMe4F (18.6 mg, 0.2 jumol, 2 equiv) and the appropriate aryi chloride or nitroarene substrate (0.1 nimol, 1 equiv) were weighed into a 4 mL vial equipped with a micro stirbar. DMF (0.5 mL) was added, and the viai was removed from the drybox and stirred at room temperature unless otherwise noted for 24 hours. The reaction was cooled to room temperature and an internal standard (1, 3, 5-trifluorobenzene, 100 iL of a 0.5 M solution in toluene) was added. An aliquot was removed for analysis by 59F NMR spectroscopy and GCMS.General procedure: In a 10 mL seal tube, 2-fluorobenzonitrile (143 muL, 1.38 mmol), sodium azide (0.1 g, 1.54 mmol), TEA.HCl (0.21 g, 1.54 mmol) were heated at 120 C for 6 h. Once benzonitrile is completely consumed, reaction is cooled down and ice-cold 1N HClaq (10 mL) was added to the crude, precipitates formed are filtered, washed with cold water and dried under vacuum to obtain desired product. (0.16 g, 78%)

Molecular Weight:122.10
XLogP3:1
Hydrogen Bond Acceptor Count:3
Exact Mass:122.02802627
Monoisotopic Mass:122.02802627
Topological Polar Surface Area:36.7
Heavy Atom Count:9
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes