[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24](F)=[CH:23][C:22]=3F)[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:29].[ClH:30]>C(Cl)Cl.O1CCOCC1>[Cl:30][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[C:18]2[C:13]=1[CH2:12][CH2:11][C:10](=[O:29])[N:9]2[C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8].[ClH:1]Compound 1 (0.95 g, 1.68 mmol), 1a (0.76 g, 2.19 mmol), Pd(PPh3)4 (0.19 g, 0.17 mmol) and LiCl (0.28 g, 6.72 mmol) in 30 mL of dioxane were purged with nitrogen for 3 times and the solution was heated at 108° C. for 20 h. Solvent was removed by vacuum and the residue was dissolved in EtOAc. The organic layer was washed with aqueous NaHCO3, dried with Na2SO4 and was purified by flash chromatography EtOAc/hexane=1:3 to give compound 2. Step B: Compound 2 (1.00 g, 1.68 mmol) in 10 mL of CH2Cl2 was added solution of HCl in dioxane (6.7 mL as 4M solution) and the resulting solution was stirred at rt for 24 h. Volatiles were removed by vacuum to give compound 6 as HCl salt. Mass spectrum (ESI), 499 (M+1).
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