反应详情

Triethylamine (0.168 mL, 1.21 mmol) then ethyl chloroformate (0.115 mL, 1.21 mmol) were added to N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-5-chloroindole-2-carboxamide (Example 2, 437 mg, 1.10 mmol) in anhydrous THF (10 mL) at 0° C. followed by stirring for 1 h. LiBH4 (2.0 M in THF, 0.69 mL, 1.37 mmol) was added slowly and the mixture stirred for a further 30 min. The reaction was carefully quenched with 1M HCl (50 mL) and EtOAc (100 mL) and the organic layer was further washed with sat. aqueous NaHCO3 (30 mL), brine (30 mL), dried (MgSO4), filtered and evaporated. The residue was triturated with refluxing Et2O (10 mL) and after cooling the solid was filtered and dried to afford the title compound (325 mg, 77%) a white solid.

1. stirringthe mixture stirred for a further 30 min
2. customThe reaction was carefully quenched with 1M HCl (50 mL) and EtOAc (100 mL)
3. washthe organic layer was further washed with sat. aqueous NaHCO3 (30 mL), brine (30 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. customThe residue was triturated with refluxing Et2O (10 mL)
8. temperatureafter cooling the solid
9. filtrationwas filtered
10. customdried