Potassium Carbonate → HCID 67520579, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-{4-[6-amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (BB8) (75 mg, 0.16 mmol), 4-bromo-2-iodo-6-trifluoromethoxy-1,3-benzothiazole (81 mg, 0.19 mmol), potassium carbonate (66 mg, 0.48 mmol), Pd(PPh3)4 (18 mg, 0.016 mmol) in DME (3 mL) and H2O (1 mL) was evacuated and refilled with N2 (3×), then it was heated at 80° C. for 2 h. The mixture was diluted with EtOAc (30 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hex.:EtOAc=30:70→15:85) to give the Boc-protected title compound as a yellow solid, MS (ES+): m/z=639/641 (1/1) [MH+]. This material was dissolved in DCM (1 mL) and treated with 1M HCl in diethyl ether (3 mL, 3 mmol). The resulting mixture was stirred at room temperature overnight. The solid that formed was filtered off, washed with DCM, and dried in vacuo to give the title compound as yellow solid. MS (ES+): m/z=538.98/540.96 (1/1) [MH+].

Provenance & Evidence