Methyl Methacrylate → HCID 89740370, Verbindung

Temperatur

110 °C

To a solution of 2-iodopyridin-3-amine (500 mg, 2.27 mmol), cuprous oxide (32 mg, 0.23 mmol), cesium carbonate (740 mg, 2.27 mmol) in N,N-dimethylformamide (100 mL) was added methyl methacrylate (290 mg, 2.5 mmol). The reaction solution was stirred at 110° C. for 12 hours. Then the reaction mixture was cooled to room temperature and added sodium hydride (60% in oil, 91 mg, 2.27 mmol) under ice bath. The resulting mixture was stirred at room temperature for half an hour. Then (1-bromoethyl)benzene (418 mg, 2.27 mmol) was added. Then the mixture was stirred at room temperature for 1 hour. After the reaction was completed, it was quenched with water (100 mL), and extracted with ethyl acetate (50 mL×3). The combined organic phase were washed with water (20 mL×3) and brine (20 mL), dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1) to give methyl 2-methyl-1-(1-phenylethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylate (80 mg, 12%). LRMS (M+H) m/z: calcd 295.14. found 295.

1. temperatureThen the reaction mixture was cooled to room temperature
2. stirringThe resulting mixture was stirred at room temperature for half an hour
3. stirringThen the mixture was stirred at room temperature for 1 hour
4. customit was quenched with water (100 mL)
5. extractionextracted with ethyl acetate (50 mL×3)
6. washThe combined organic phase were washed with water (20 mL×3) and brine (20 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated
9. custompurified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1)

ORD-Eintrag

ord-faa7cf871f95403bb4cfd98a4794c6c2

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09371331B2