反应详情

温度

80 °C

3-((2-Cyclopentyl-1-oxoisoindolin-5-yloxy)methyl)phenylboronic acid (30 mg, 0.08 mmol), 3-iodo-4-methoxybenzoic acid (19.7 mg, 0.07 mmol), K2CO3 (29 mg, 0.21 mmol) and PdCl2(PPh3)2 (6.2 mg, 0.009 mmol) were dissolved in a mixture of toluene-MeOH (1.1 mL:0.1 mL) and heated at 80° C. for 1.5 hours. The mixture was filtered through celite washed with water and solvent was removed was evaporated in vacuo. The resulted crude material was acidified with 2 M HCl, extracted into EtOAc and dried over anhyd. Na2SO4, evaporated solvent in vacuo to obtain the crude acid which was purified using automated prep-HPLC to yield the desired compound 4.2 mg, 13%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.93 (d, J=8.2 Hz, 1H), 7.82 (s, 1H), 7.55-7.42 (m, 5H), 7.21-7.18 (m, 2H), 7.10 (dd, J=8.7 Hz, J=2.3 Hz, 1H), 5.23 (s, 2H), 4.54-4.46 (m, 1H), 4.37 (s, 2H), 3.84 (s, 3H), 1.85-1.80 (m, 2H), 1.71-1.56 (m, 6H). LRMS calcd. for C28H27NO5 [M+H]+ 458 found: 458.

1. filtrationThe mixture was filtered through celite
2. washwashed with water and solvent
3. customwas removed
4. customwas evaporated in vacuo
5. customThe resulted crude material
6. extractionextracted into EtOAc
7. customdried over anhyd
8. customNa2SO4, evaporated solvent in vacuo
9. customto obtain the crude acid which
10. customwas purified