Sodium Carbonate → HCID 86594579, compound

Participants

Reaction Conditions

Reaction Steps

N-(cyanomethyl)-4-methyl-2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]thio}pentanamide (1.64 g, 4.22 mmol) and tert-butyl 4-bromobenzylcarbamate (1.33 g, 4.64 mmol) were mixed in DMF (12 mL). After addition of sodium carbonate (7.4 mL of a 2.0 M solution, 14.8 mmol), the reaction flask was thoroughly degassed with dry nitrogen. PdCl2dppf (103 mg, 0.13 mmol) was added and the reaction mixture was heated at 80° C. for 4 h. Aqueous sat. NaHCO3 was added, the product was extracted with EtOAc (3×), dried over MgSO4, concentrated in vacuo, and purified by flash chromatography (40% EtOAc/hexanes) to afford tert-butyl {4′-[(1-{[(cyanomethyl)amino]carbonyl }-3-methylbutyl)thio]-1,1′-biphenyl-4-yl}methylcarbamate.

Provenance & Evidence