Potassium Acetate → HCID 58541883, compound

Participants

Reaction Conditions

Reaction Steps

To a high pressure vessel are added 2-amino-3-hyroxymethyl-5-bromopyridine (90 mg, 0.44 mmol), bis(pinacolato)diboron (135 mg, 0.53 mmol) and KOAc (131 mg, 1.33 mmol) in 10 mL of 1,4-dioxane. The solution is degassed with nitrogen for 10 minutes, followed by the addition of PdCl2(dppf) (36 mg, 0.04 mmol). The reaction mixture is warmed to 80° C. and stirred for 1 hour. After this time a solution of 5-bromo-1-tert-butyl-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-1H-benzimidazole (226 mg, 0.53 mmol) and additional PdCl2(dppf) (16 mg, 0.02 mmol) in DMF (1 mL) and 2M Na2CO3 (0.1 mL) are added. The reaction is heated at 80° C. for 12 hours, then cooled to room temperature and poured into water. The mixture is extracted with EtOAc (3×) and the combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 0-8% MeOH/CH2Cl2) and preparative TLC (0.5 mm silica gel, 8% MeOH/CH2Cl2) gives the title compound (15 mg, 7%). LCMS (ESMS): m/z 469.20 (M++1)

Provenance & Evidence