Sodium Iodide → HCID 18476406, compound

Sodium hydride (60% dispersion in oil, 0.38 g) was added to the mixed solution of ethyl 3-(indol-3-yl)propionate (1.8 g) in DMF (20 ml) and THF (20 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 10 minutes, to which were added 2,4-dichlorobenzyl bromide (1.8 g) and sodium iodide (0.3 g). The reaction mixture was stirred at room temperature for 3 hours and then poured into water, and the mixture was extracted with IPE. The organic layer was washed with water, then dried and concentrated. The residue was dissolved in ethanol (30 ml), which was stirred at 50° C. for 2 hours in the presence of water (10 ml) and sodium hydroxide (1 g). The reaction mixture was concentrated, made acidic, and then extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was recrystallized from ethyl acetate-IPE to obtain the entitled compound (2.4 g).

1. temperaturecooling
2. stirringThe reaction mixture was stirred at room temperature for 3 hours
3. extractionthe mixture was extracted with IPE
4. washThe organic layer was washed with water
5. customdried
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in ethanol (30 ml)
8. stirringwhich was stirred at 50° C. for 2 hours in the presence of water (10 ml) and sodium hydroxide (1 g)
9. concentrationThe reaction mixture was concentrated
10. extractionextracted with ethyl acetate
11. washThe organic layer was washed with water
12. customdried
13. concentrationconcentrated
14. customThe residue was recrystallized from ethyl acetate-IPE

ORD record

ord-81ff317e188b48c8b91f6cf4672be8ef

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329389B1