KOtBu THF → HCID 59471423, compound

Temperature

-10 °C

2.5 ml of 1M KOtBu THF solution was added to 20 mL of THF and the solution was cooled at −10° C. A solution of 3-(1-tert-butoxycarbonylmethyl-6-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-propionic acid ethyl ester (0.73 g) in 4 mL of THF was added over 2 min. After stirring for 15 min at −10° C., 3 mL of 1 N HCL was added, followed by 10 mL brine. The mixture was extracted with 40 mL of EtOAc, dried over Na2SO4, filtered, and concentrated. The residue was dissolved in 30 mL of toluene and added 1 g of silica gel, and the resulting mixture was heated to reflux for 3 h. After cooling, the reaction mixture was filtered and concentrated. The residue was purified by silica gel chromatography eluted with 40% EtOAc/hexane to give 0.3 g of the title product as beige solid.

1. addition3 mL of 1 N HCL was added
2. extractionThe mixture was extracted with 40 mL of EtOAc
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in 30 mL of toluene
7. additionadded 1 g of silica gel
8. temperaturethe resulting mixture was heated
9. temperatureto reflux for 3 h
10. temperatureAfter cooling
11. filtrationthe reaction mixture was filtered
12. concentrationconcentrated
13. customThe residue was purified by silica gel chromatography
14. washeluted with 40% EtOAc/hexane

ORD record

ord-3656d13993ee4465b20aafa1d3de7771

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772312B2