Br[C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:12][N:13]1C(=O)CCC1>[C-]#N.[C-]#N.[Zn+2].[Zn].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]>[CH3:11][C:8]1[C:7]2[NH:6][CH:5]=[CH:4][C:3]=2[C:2]([C:12]#[N:13])=[CH:10][CH:9]=1To a solution of 306 (300 mg, 1.43 mmol) in NMP (3 mL) under argon atmosphere were added Zn(CN)2 (167 mg, 1.43 mmol), zinc powder (18 mg, 0.28 mmol), Pd2(dba)3 (198 mg, 0.21 mmol), and dppf (237 mg, 0.42 mmol). After stirring at 140° C. for 18 h, the mixture was cooled and partitioned between ethyl EtOAc (200 mL) and water (50 mL). The organic layer was separated, washed with brine, dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified by SiO2 chromatography eluting with 15% EtOAc/petroleum ether to afford 222 mg (85%) of 7-methyl-1H-indole-4-carbonitrile (308) as yellow solid.
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