Sodium Carbonate → HCID 86643696, compound

Participants

Reaction Conditions

Reaction Steps

(S)-5-(3-Bromophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (243 mg, 0.599 mmol) obtained in Step 1 of Example 13 was dissolved in 1,4-dioxane (7 mL), and the mixture was stirred at 100° C. for hours after adding bis(pinacolato)diboron (0.380 g, 1.50 mol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 98.0 mg, 0.120 mmol), and potassium acetate (0.295 g, 3.00 mmol). The reaction mixture was filtered through sellite, and the filtrate was diluted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography. The resulting crude product was dissolved in 1,4-dioxane/water=4/1 (12.5 mL), and the mixture was stirred at 100° C. for 3 hours after adding 2-chloro-4-iodopyridine (216 mg, 0.902 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf); 49.0 mg, 0.060 mmol), and sodium carbonate (191 mg, 1.80 mmol). The reaction mixture was then filtered through sellite, and the filtrate was extracted with ethyl acetate. The organic layer was then washed with saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was purified by silica gel column chromatography to give 5-[3-(2-chloropyridin-4-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro5,8,10,10b-tetraazabenzo[e]azulen-6-one (113 mg, 43% (2 steps)).

Provenance & Evidence