C[CH2:2][N:3](C(C)C)C(C)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Br[C:45]1[CH:54]=[CH:53][C:52]([N+:55]([O-:57])=[O:56])=[C:51]2[C:46]=1[CH:47]=[CH:48][CH:49]=[N:50]2.O>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2]>[N+:55]([C:52]1[C:51]2[N:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:45]([C:2]#[N:3])=[CH:54][CH:53]=1)([O-:57])=[O:56]
Zn(CN)2 (739 mg, 6.3 mmol), DIPEA (0.41 ml, 2.37 mmol), X-phos (225 mg, 0.47 mmol) and Pd2 (dba)2 (90 mg, 0.16 mmol) were added to a degassed (with argon) solution of 5-bromo-8-nitroquinoline 470 (400 mg, 1.58 mmol) in DMF (4 ml) and the mixture was heated at 100° C. in microwave for 20 min. After cooling, the mixture was poured into water and the aqueous phase was extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (96:4) as the eluent to give the title compound (230 mg, 63%).
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