COC(=O)C1C=CC(C#C[C:12]2[CH:13]=[C:14]([CH:26]3[CH2:28]C3)[C:15]3O[C:19]4(CC4)[CH2:18][C:17]([CH3:24])([CH3:23])[C:16]=3[CH:25]=2)=CC=1F.[C:31](O)(=O)[C:32]1[CH:37]=CC=CC=1.[CH2:40]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][C:47](I)=[CH:46][CH:45]=1)[CH3:41].C([N:54](CC)CC)C.O1CCCC1>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH2:40]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][C:47]([C:28]#[C:26][C:14]2[CH:15]=[C:16]3[C:25](=[CH:12][CH:13]=2)[N:54]([CH:32]2[CH2:31][CH2:37]2)[CH2:19][CH2:18][C:17]3([CH3:23])[CH3:24])=[CH:46][CH:45]=1)[CH3:41]Following general procedure F and using 1-cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydro quinoline (Intermediate 53, 0.11 g, 0.43 mmol), ethyl-4-iodo-benzoate (Reagent A, 0.11 g, 0.9 mmol), triethyl amine (3 mL), tetrahydrofuran(3 mL), copper(I)iodide(0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.060 g, 0.085 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.05 g, 31%).
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