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SNAr (Br)

(Cyanide)







Examples:


Example 1



A mixture of the SM (150 mg, 0.36 mmol), TBAF (281 mg, 1.08 mmol), and TMSCN (107 mg, 1.08 mmol) in DMF (3 mL) was stirred at 100 C for 1 h. After cooling to RT, the mixture was purified by Prep HPLC (5-95% MeOH/H2O with 0.05% NH4OH) to provide the product as a white solid. [50 mg, 38%]


[Patent Reference: WO2016011390, page 151, (20.2 MB)]



Example 2



To a solution of the SM (3.5 g, 7.14 mmol) in pyridine (10 mL) was added CuCN (636 mg, 7.14 mmol) at RT. The reaction mixture was stirred at 100 C for 16 h. After concentration, the residue was purified by silica gel column chromatography (10:1 PE/EtOAc) to provide the product as a white solid. [550 mg, 19%]


[Patent Reference: WO2016011390, page 133, (20.2 MB)]