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)]