Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([I:10])[N:4]2[N:3]=1.[CH2:11]([N:13]1[CH:17]=[C:16](B(O)O)[CH:15]=[N:14]1)[CH3:12].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>[CH2:11]([N:13]1[CH:17]=[C:16]([C:2]2[S:6][C:5]3=[N:7][CH:8]=[C:9]([I:10])[N:4]3[N:3]=2)[CH:15]=[N:14]1)[CH3:12]
A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.18 g, 0.546 mmol, 1 eq), 1-ethyl-1H-pyrazole-4-boronic acid, pinacol ester (0.145 g, 0.655 mmol, 1.2 eq), Pd(PPh3)2Cl2 (0.077 g, 0.109 mmol, 0.2 eq) and 2M aq Na2CO3 (1 mL) in dioxane (3 mL) was refluxed for 2 h. The solvent was evaporated and the residue was treated with water. The suspension was filtered off (avoid taking the heavier reddish solid) and washed with water. The solid (110 mg) was used in the next step of the synthesis with no further treatment. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.98 min, [M+H]+ m/z 345.9.
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