Sodium Carbonate → N'-{4-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]phenyl}-N,N-dimethyl-methanesulfonimidamide

Participants

Reaction Conditions

Reaction Steps

A mixture of (3R,3aR,6R,6aR)-6-(6-chloro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (1.00 g), N′-(4-bromophenyl)-N,N-dimethyl-methanesulfonimidamide (484 mg), Na2CO3 (2 M aqueous solution, 1.98 mL), and ethanol (8 mL) is purged for 5 minutes with argon. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II)-CH2Cl2-complex (PdCl2(dppf)×CH2Cl2) (130 mg) is added and the mixture is stirred over night at 70° C. The reaction mixture concentrated in vacuo and the residue is purified by preparative HPLC to give the title compound. LC (method 1): tR=1.13 min; Mass spectrum (ESI+): m/z=700 [M+H]+.

Provenance & Evidence