[F:1][C:2]1[C:7](I)=[CH:6][C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][N:3]=1.[CH3:12][N:13](C=O)C>CCOC(C)=O.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[N:3]=[CH:4][C:5]([CH:9]([CH3:11])[CH3:10])=[CH:6][C:7]=1[C:12]#[N:13]To a mixture of 2-fluoro-3-iodo-5-isopropylpyridine and 485 mg (4.13 mmol) of Zn(CN)2 in 15 mL of DMF (degassed) was added 360 mg (0.312 mmol) of Pd(PPh3)4. The mixture was heated at 80° C. under Ar for 19 h. The mixture was diluted with EtOAc, and the organic layer was washed with 10% NH4OH (2×10 mL), H2O (3×), and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (5% Et2O/hexanes) provided 384 mg of pure 2-fluoro-5-isopropylnicotinonitrile as a yellow liquid.
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