反应详情

温度

90 °C

2-(4-bromophenyl)sulfonyl-N,N-dimethyl-ethanamine (181.8 mg, 0.6221 mmol) was dissolved in dioxane (2 mL) and bis(pinacolato)diboron (237.0 mg, 0.9332 mmol) and potassium acetate (183.1 mg, 1.866 mmol) were added. The reaction mixture was degassed and filled with nitrogen (5×) then Pd(dppf)Cl2.CH2Cl2 (50.80 mg, 0.06221 mmol) was added and the reaction heated to 90° C. for 2 hours. The reaction mixture was cooled to ambient temperature and diluted with DMF (2 mL). [4-[5-(3-amino-6-bromo-pyrazin-2-yl)-1,3,4-oxadiazol-2-yl]phenyl]acetate (234 mg, 0.6221 mmol), Na2CO3 (933.0 μL of 2 M aqueous solution, 1.866 mmol) and Pd(PPh3)2Cl2 (43.67 mg, 0.06221 mmol) were added and the reaction heated at 150° C. under microwave conditions for 30 minutes. The reaction mixture was partitioned between EtOAc (5 mL) and water (5 mL) and any precipitate removed by filtration. The layers were separated and the aqueous layer extracted with EtOAc (3×5 mL) and the combined organic extracts dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated form EtOAc/MeOH to give the title compound as a brown solid (44.3 mg, 15%); 1H NMR (400 MHz, DMSO) d 2.07 (s, 6H), 2.56 (t, 2H), 3.52 (t, 2H), 7.03 (d, 2H), 7.87 (br s, 2H), 8.02 (dd, 4H), 8.38 (d, 2H), 9.05 (s, 1H) and 10.44 (s, 1H) ppm; MS (ES+) 467.2

1. customThe reaction mixture was degassed
2. additionfilled with nitrogen (5×)
3. temperatureThe reaction mixture was cooled to ambient temperature
4. temperaturethe reaction heated at 150° C. under microwave conditions for 30 minutes
5. customThe reaction mixture was partitioned between EtOAc (5 mL) and water (5 mL)
6. customany precipitate removed by filtration
7. customThe layers were separated
8. extractionthe aqueous layer extracted with EtOAc (3×5 mL)
9. dry with materialthe combined organic extracts dried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was triturated form EtOAc/MeOH