Potassium Carbonate → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (26.94 mg, 0.071 mmol), 3-bromo-7-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine (20.0 mg, 0.047 mmol), potassium carbonate (19.7 mg, 0.14 mmol) in DME (2.0 mL) and H2O (0.40 mL) was added Pd(PPh3)4 (2.8 mg, 0.0024 mmol) under Nitrogen. The resulting mixture was refluxed at 100° C. for 30 min. LC-MS indicated completion of reaction. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography (2% MeOH in DCM). MS (ES+): m/z 590.07, 592.08 (MH+). HPLC: tR=3.48 min (ZQ3, polar—5 min). The product purified above was then dissolved in 2 mL dioxane, to this solution was added solution of 4 N HCl in dioxane (1 mL) at r.t., the resulting mixture was stirred at r.t. for 1.5 h. LC-MS indicated completion of reaction. The solvent was removed under reduced pressure to give the title compound as HCl salt. The 1H NMR spectrum matches that of Example 5.

Provenance & Evidence