Sodium Carbonate → HCID 17981744, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-methoxybenzyl)-2-tert-butyldimethylsilyloxymethyl-4-(phenyl)-5-iodoimidazole (50 mg, 0.0935 mmol) in dry toluene (0.8 mL) previously bubbled with a stream of nitrogen, add PdCl2(PPh3)2 (4.5 mg, 0.00641 mmol) in one portion. After 5 minutes, add a suspension of 1-isopropylsulfonyl-2-amino-benzimidazole-6-boronic acid (40 mg, 0.141 mmol) in ethanol (0.8 mL) previously bubbled with a stream of nitrogen, followed by sodium carbonate (2M in water, 0.32 mL, 0.640 mmol). Stir the mixture for 2.5 hours at 100° C., cool to room temperature, dilute with 10% HCl (5 mL), extract with EtOAc (15 mL), dry (Na2SO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2, CH2Cl2/MeOH 19:1→5:1), dissolve the material obtained in MeCN (0.5 mL), and treat with HF (48% in H2O, 0.12 mL, 3.31 mmol) at room temperature for 4 hours. Dilute the mixture with EtOAc (15 nm), wash with saturated NaHCO3 (5 mL), dry (Na2SO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2, CH2Cl2/MeCN/MeOH 85:15:5) to provide 18 mg (36% yield). MS (MS+): m/z=532 (M+H)+

Provenance & Evidence