Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.O.[CH3:12][N:13](C=O)C>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.Cl[Pd]Cl.[Fe+2].[C-]#N.[Zn+2].[C-]#N.[Zn]>[NH:8]1[C:4]2[CH:5]=[N:6][CH:7]=[C:2]([C:12]#[N:13])[C:3]=2[CH:10]=[CH:9]1A mixture of 4-bromo-1H-pyrrolo[2,3-c]pyridine (320 mg, 1.62 mmol), Pd(dppf)Cl2 (131 mg, 0.179 mmol), zinc cyanide (190 mg, 1.62 mmol), and zinc powder (21 mg, 0.324 mmol) in DMF (20 mL) was stirred at 120° C. for 2 h. The reaction mixtue was cooled to RT and H2O (100 mL) was added. The reaction mixture extracted with EtOAc (3×50 mL). The organic layers were concentrated tinder reduced pressure and the crude residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (1:1) to afford 232 mg (99.8%) of 1H-pyrrolo[2,3-c]pyridine-4-carbonitrile as yellow solid: MS (ESI) m/z: 144.2 [M+1]+.
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