I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH3:13][O:12][CH2:11][CH2:10][CH2:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1A mixture of the compound of step 1 (8.00 g, 27.4 mmol), indole (3.21 g, 27.4 mmol), copper(I) iodide (522 mg, 2.74 mmol), L-proline (636 mg, 5.48 mmol) and potassium carbonate (7.68 g, 54.8 mmol) in DMSO (50 ml) was stirred for 26 h at 125° C. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by preparative HPLC. The eluate was lyophilized overnight to give 3.10 g of the title compound.
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