Synthese
Step 1: 4-(2-chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine (Compound 0113, 800 mg, 1.86 mmol), pinacol ester of 1H-indazole-4-boronic acid (0107-3, 500 mg, 2.04 mmol), sodium bicarbonate (470 mg. 5.58 mmol), sodium bicarbonate (470 mg, 5.58 mmol), and bis(triphenylphosphine)palladium(II) chloride (80 mg, 0.093 mmol) were dissolved in a solvent mixture of toluene (20 mL), ethanol (12 mL), and water (5.6 mL). The reaction system was replaced by nitrogen and then heated at 120 °C for 1 h under microwave radiation. After completion of the reaction, the reaction mixture was partitioned between dichloromethane and water. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: dichloromethane containing 2% methanol, v/v) to afford 2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (Compound 0114, 350 mg, 37% yield) as a white solid with a melting point of 148-149 °C. LC -MS: m/z 514 [M+H]+; 1H NMR (400 MHz, CDCl3): δ 2.70 (t, J = 4.4 Hz, 4H), 2.81 (s, 3H), 3.13 (t, J = 4.4 Hz, 4H), 3.92 (m, 6H), 4.09 (t, J = 5.6 Hz, 4H), 7.41 (s, 1H), 7.50 (m, 1H), 7.59 (d, J = 8.4 Hz, 1H), 8.28 (d, J = 6.8 Hz, 1H), 9.00 (s, 1H), 10.32 (br s, 1H).
![4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-INDAZOLE](/CAS/GIF/885618-33-7.gif)
![2-CHLORO-6-(4-METHANESULFONYL-PIPERAZIN-1-YLMETHYL)-4-MORPHOLIN-4-YL-THIENO[3,2-D]PYRIMIDINE](/CAS/GIF/885675-66-1.gif)
