Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([I:10])[N:4]2[N:3]=1.[N:11]1([S:17]([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[I:10][C:9]1[N:4]2[C:5]([S:6][C:2]([C:23]3[CH:24]=[CH:25][C:20]([S:17]([N:11]4[CH2:12][CH2:13][O:14][CH2:15][CH2:16]4)(=[O:18])=[O:19])=[CH:21][CH:22]=3)=[N:3]2)=[N:7][CH:8]=1A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (200 mg, 0.44 mmol), 4-(4-morpholinylsulfonyl)phenylboronic acid (144 mg, 0.52 mmol), PdCl2(PPh3)2 (60 mg, 0.088 mmol) and 2M aq Na2CO3 (1.2 mL) in dioxane (8 mL) was heated at 90° C. for 18 h. The solvent was removed in vacuo and the residue was triturated from EtOAc and filtered. The filtrate was evaporated and the residue was recrystallyzed from MeOH to give the desired product (89 mg, 31%) as a brown solid.
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