تفاعل #563206
ord-46e3d813ceef4f8e8be785cef45bbcdf
معادلة التفاعل
المتفاعلات
المذيبات
ظروف التفاعل
المعالجة
- 1درجة الحرارةAfter cooling to room temperature
- 2أخرىThe reaction mixture was irradiated (microwave) at 120° C. for 2 h
- 3درجة الحرارةThe reaction mixture was cooled
- 4درجة الحرارةcooled to room temperature
- 5ترشيحfiltered through Na2SO4
- 6أخرىThe contents were purified directly by silica gel chromatography (eluent: 5% MeOH/CH2Cl2)
الإجراء التجريبي
6-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one (200 mg, 0.881 mmol) (J. Med. Chem. 2003; 46; 9; 1627-1635), bis(pinacolato)diboron (268 mg, 1.057 mmol), Pd(dppf) (35.7 mg, 0.044 mmol) and potassium acetate (259 mg, 2.64 mmol) were suspended in 1,4-Dioxane (8 mL), and stirred with heating at 100° C. for 1 h. After cooling to room temperature, 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (329 mg, 0.881 mmol), bis(triphenylphosphine)palladium(II) chloride (71.9 mg, 0.088 mmol) and sodium bicarbonate (222 mg, 2.64 mmol) were added, followed by DME (5 mL) and water (3 mL). The reaction mixture was irradiated (microwave) at 120° C. for 2 h. The reaction mixture was cooled cooled to room temperature and filtered through Na2SO4. The contents were purified directly by silica gel chromatography (eluent: 5% MeOH/CH2Cl2) to furnish the desired product as a grey solid after evaporation and precipitation from warm EtOAc/MeOH (1:9). The product was collected as 55 mg (13%). LCMS E-S (M+H)=486.3 1H NMR (400 MHz, DMSO-d6) δ ppm 11.57 (br. s., 1H), 10.74 (s, 1H), 8.99 (d, J=2.27 Hz, 1H), 8.93 (t, J=4.93 Hz, 1H), 8.44 (d, J=1.77 Hz, 1H), 8.37 (s, 1H), 8.16 (s, 1H), 5.91 (s, 1H), 5.29-5.40 (m, 1H), 4.42 (d, J=5.05 Hz, 2H), 3.04 (t, J=7.58 Hz, 2H), 2.53-2.62 (m, 2H), 2.23 (s, 3H), 2.13 (s, 3H), 1.54 (d, 6H).