Triethylamine → HCID 71295154, Verbindung

4-chlorobutanoyl chloride (670 mg, 4.76 mmol) was added dropwise to a 0° C. solution of ethyl 6-amino-5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate and Et3N (1.0 mL) in CH2Cl2 (10 mL) under N2 atmosphere. The resulting reaction was allowed to stir at room temperature for 16 hours, then the reaction mixture was concentrated in vacuo. The resulting resulting residue was dissolved in CH3CN (10 mL), and then K2CO3 (658 mg, 4.76 mmol) and KI (263 mg, 1.59 mmol) was added and the mixture was heated to reflux and allowed to stir at this temperature for 16 hours. After being cooled to room temperature, the mixture was diluted with water and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue obtained was purified using column chromatography (eluted with petroleum ether:EtOAc=2:1) to provide ethyl 5-bromo-2-(4-fluorophenyl)-6-(2-oxopyrrolidin-1-yl)benzofuran-3-carboxylate (280 mg, yield: 40%). 1H-NMR (CDCl3, 400 MHz) δ 8.32 (s, 1H), 8.04˜8.07 (m, 2H), 7.48 (s, 1H), 7.17˜7.21 (m, 2H), 4.42˜4.43 (m, 2H), 3.82˜3.86 (m, 2H), 2.61˜2.65 (m, 2H), 2.27˜2.31 (m, 2H), 1.40˜1.44 (m, 3H). MS (M+H)+: 446/448.

1. customThe resulting reaction
2. concentrationthe reaction mixture was concentrated in vacuo
3. customThe resulting resulting residue
4. temperaturethe mixture was heated
5. temperatureto reflux
6. stirringto stir at this temperature for 16 hours
7. temperatureAfter being cooled to room temperature
8. extractionextracted with EtOAc
9. extractionThe organic extract
10. washwas washed with brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe residue obtained
15. customwas purified
16. washcolumn chromatography (eluted with petroleum ether:EtOAc=2:1)

ORD-Eintrag

ord-c83b6f1ceba94e4ead8052247bb8bc8c

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09265773B2