Acetic Acid → HCID 22556753, compound

Temperature

22 °C

Add allylamine (2.50 mL, 33.1 mmol), acetic acid (3.4 mL), and sodium triacetoxyborohydride (5.85 g, 27.6 mmol) to a solution of indole-7-carboxaldehyde (4.00 g, 27.6 mmol) in 1,2-dichloroethane (120 mL) at 20-24° C. and stir the resulting mixture at 20-24° C. for 5 hours. Add an additional 1.5 g (7.1 mmol) of sodium triacetoxyborohydride and stir the resulting mixture overnight. Dilute the mixture with dichloromethane (300 mL), wash carefully with aqueous sodium bicarbonate (100 mL), and separate the layers. Wash the organic layer sequentially with water (100 mL) and saturated aqueous sodium chloride (100 mL), dry over sodium sulfate, filter, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 10-30% ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound as a light yellow oil (4.21 g, 82%).

1. stirringstir the resulting mixture overnight
2. washwash carefully with aqueous sodium bicarbonate (100 mL)
3. customseparate the layers
4. washWash the organic layer sequentially with water (100 mL) and saturated aqueous sodium chloride (100 mL)
5. dry with materialdry over sodium sulfate
6. filtrationfilter
7. concentrationconcentrate under reduced pressure
8. washeluting with 10-30% ethyl acetate in hexanes
9. additionCombine fractions containing product
10. concentrationconcentrate them under reduced pressure

ORD record

ord-1e52948c74fc45c28ced0eff0d5eea89

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022065B2