Sodium Carbonate → (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

Participants

Reaction Conditions

Reaction Steps

A mixture of (3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (2.00 g), 1,4-benzenediboronic acid dipinacol ester (2.38 g), Na2CO3 (2 M aqueous solution, 5.42 mL), and 1,4-dioxane (15 mL) is purged for 5 minutes with argon. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II)-CH2Cl2-complex (PdCl2(dppf)×CH2Cl2) (206 mg) is added and the mixture is stirred over night at 70° C. The reaction mixture is partitioned between water and ethyl acetate. The organic phase is washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 99:1→97:3) to give the title compound. LC (method 1): tR=1.27 min; Mass spectrum (ESI+): m/z=630 [M+H]+.

Provenance & Evidence