Br[C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.O.[CH3:13][N:14]1C(=O)CCC1>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].[C-]#N.[C-]#N.[Zn+2].[Zn]>[CH3:11][C:10]1[CH:9]=[CH:8][C:7]2[NH:6][CH:5]=[CH:4][C:3]=2[C:2]=1[C:13]#[N:14]A mixture of 300 (150 mg, 0.714 mmol), Pd2(dba)3 (131 mg, 0.143 mmol), dppf (159 mg, 0.286 mmol), Zn(CN)2 (84 mg, 0.714 mmol), and zinc (4.6 mg, 0.0714 mmol) in NMP (10 mL) under nitrogen atmosphere was heated at 145° C. for 18 h. The reaction mixture was poured into water (50 mL) and extracted with EtOAc (20 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated to dryness. The crude was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (3:1) to afford 54 mg (48.5%) 5-methyl-1H-indole-4-carbonitrile (302) as yellow solid: MS (ESI) m/z=157.1 (M+1).
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