反应详情

温度

100 °C

To a slurried solution of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (4.3 g, 13 mmol), 4-methoxy-2-formylphenylboronic acid (3.0 g, 17 mmol) and LiCl (2.2 g, 51 mmol) in EtOH/toluene (1:1, 100 mL) was added Pd(PPh3)4 (1.4 g, 1.3 mmol) and then 1M Na2CO3 (aq.) (32 mL, 32 mmol). The reaction solution was flushed with nitrogen and heated at 100° C. for 3 h and cooled to rt. The reaction was concentrated to remove EtOH, diluted with H2O (200 mL) and extracted with EtOAc (2× 150 mL). The combined organics were washed with brine (100 mL), dried (MgSO4), filtered and concentrated to dryness. The residue was triturated with CH2Cl2 and the solids were collected by filtrated and washed with Et2O and CH2Cl2 to yield methyl 11-cyclohexyl-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxylate (3.0 g, 8.0 mmol, 63%) as a yellow solid which was used without further purification. LCMS: m/e 374 (M+H)+, ret time 3.09 min, column B, 3 minute gradient.

1. customThe reaction solution was flushed with nitrogen
2. temperaturecooled to rt
3. concentrationThe reaction was concentrated
4. customto remove EtOH
5. additiondiluted with H2O (200 mL)
6. extractionextracted with EtOAc (2× 150 mL)
7. washThe combined organics were washed with brine (100 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated to dryness
11. customThe residue was triturated with CH2Cl2
12. customthe solids were collected
13. filtrationby filtrated
14. washwashed with Et2O and CH2Cl2