[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[N:9][C:10]=2I)[CH:7]=1.O.[CH3:22][N:23](C=O)C>[NH4+].[OH-].[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[N:9][C:10]=2[C:22]#[N:23])[CH:7]=1To a solution of the intermediate from Step H (4.32 g, 10.18 mmol) in DMF (50 mL) was added zinc cyanide (2.39 g, 20.35 mmol), Pd2 dba3 (0.47 g, 0.51 mmol), DPPF (0.564 g, 1.02 mmol), and water (2.5 mL). The resulting solution was heated at 120° C. for 18 hours. The reaction was cooled to room temperature, diluted with 15% NH4OH solution (10 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. m/z=323.9 (M+H).
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