반응 #804291

반응 방정식

3-Chloro-5-methyl-2H-isoquinolin-1-one

K2CO3

→

4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoic acid

수율 79.9%

용매

DME EtOH H2O

반응 조건

후처리

1. 1
   기타the reaction mixture purged with N2 for 10 min
2. 2
   기타The reaction mixture was irradiated
3. 3
   기타a microwave (300 W, 120° C., 2 h)
4. 4
   농축The reaction mixture was concentrated in vacuo, water
5. 5
   workup.ADDITIONadded
6. 6
   여과was filtered
7. 7
   기타dried in vacuo
8. 8
   workup.DISSOLUTIONdissolved in DMF
9. 9
   세척eluting with DMF (4× column volumes)
10. 10
    기타the solvent removed in vacuo
11. 11
    기타The resulting solid was triturated with MeOH
12. 12
    여과filtered
13. 13
    기타dried

실험 절차

3-Chloro-5-methyl-2H-isoquinolin-1-one (50 mg, 0.26 mmol), 4-carboxybenezeneboronic acid (64 mg, 0.39 mmol), K2CO3 (73 mg, 0.52 mmol) and Pd(dppf)Cl2 (11 mg, 0.013 mmol) in DME/EtOH/H2O 4:0.5:1 (2.75 mL) were added to a microwave vial and the reaction mixture purged with N2 for 10 min. The reaction mixture was irradiated using a microwave (300 W, 120° C., 2 h). The reaction mixture was concentrated in vacuo, water added and the mixture acidified to pH2 with 0.2M HCl aq. A brown solid precipiated from the solution which was filtered and dried in vacuo, dissolved in DMF and passed through a Si-thiol cartridge, eluting with DMF (4× column volumes) and the solvent removed in vacuo. The resulting solid was triturated with MeOH, filtered and dried to give 4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoic acid as a beige solid (29 mg, 40%).

출처