Cl[C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.O.[CH3:12][N:13]1C(=O)CCC1>[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].[Zn]>[NH:10]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:12]#[N:13])[C:7]=2[CH:8]=[CH:9]1A mixture of 4-chloro-1H-pyrrolo[3,2-c]pyridine (500 mg, 3.28 mmol), zinc cyanide (422 mg, 3.61 mmol), Pd2(dba)3 (600 mg, 0.656 mmol), dppf (729 mg, 1.312 mmol), and Zn powder (21 mg, 0.328 mmol) in NMP (30 mL) under nitrogen was stirred at 120° C. for 18 h. The reaction mixture was cooled, poured into water (150 mL), extracted with DCM (3×50 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (1:1) as eluting solvents to afford 1H-pyrrolo[3,2-c]pyridine-4-carbonitrile as a white solid (150 mg, 32%). MS (ESI) m/z: 144.3 [M+1]+.
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