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Zinc dust (0.116 g, 1.77 mmol) and celpure P65 (0.025 g) were stirred under an argon atmosphere for 30 minutes. N,N-dimethylacetamide (0.5 mL) was added followed by 1,2-dibromoethane (0.014 mL, 0.163 mmol) and trimethylsilyl chloride (0.021 mL, 0.163 mmol). The reaction mixture was stirred at room temperature for 15 minutes, then a solution of 3-iodoazetidine-1-carboxylic acid tert-butyl ester (0.385 g, 1.36 mmol) in N,N-dimethylacetamide (1 mL) was added and stirring at room temperature was continued for 1.5 hours. The resultant mixture was filtered and the filtrate was added to a suspension of 4-chloro-2-(2,6-dichloro-4-iodophenyl)-thiazolo[5,4-c]pyridine (0.30 g, 0.68 mmol), PdCl2(dppf)•DCM (0.052 g, 0.068 mmol) and CuI (0.016 g, 0.088 mmol) in N,N-dimethylacetamide (4 mL) previously degassed with a stream of argon. The reaction mixture was heated at 80° C. for 2 hours and then allowed to cool to room temperature. The crude mixture was partitioned between diethyl ether and water and the aqueous phase was extracted with diethyl ether (×2). The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-70% Et2O in petroleum ether to afford the title compound as an off-white solid (108 mg, 34%). LCMS (Method D): RT=4.66 min, m/z: 470 [M+H+].

1. stirringstirring at room temperature
2. waitwas continued for 1.5 hours
3. filtrationThe resultant mixture was filtered
4. custompreviously degassed with a stream of argon
5. temperatureThe reaction mixture was heated at 80° C. for 2 hours
6. temperatureto cool to room temperature
7. customThe crude mixture was partitioned between diethyl ether and water
8. extractionthe aqueous phase was extracted with diethyl ether (×2)
9. washThe combined organic layers were washed with brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated under reduced pressure
12. customThe resultant residue was purified by column chromatography on silica gel eluting with 0-70% Et2O in petroleum ether