1-Methylpyrrole → HCID 86674844, Verbindung

Temperatur

110 °C

In a 500 ml round bottom flask, methyl 3-(dimethylamino)-2-((dimethylamino)methyleneamino)acrylate (1A, 24 g, 120 mmol) was dissolved in acetic acid (60 ml) and TFA (20 ml). 1-Methyl-1H-pyrrole (10.56 ml, 119 mmol) was added. The mixture was stirred at room temperature for an hour and at 110° C. for 4 hours until completion of the reaction. Volatiles were then evaporated from the reaction mixture, the residue was cooled in an ice bath. Ice cold saturated K2CO3 solution (˜200 ml) was slowly added to it. The mixture was extracted with EtOAc (3×250 ml). Combined organic layers were then washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified on silica column using hexane-EtOAc (0-100%). Desired product methyl 1-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1B, 8.5 g, 38%) was obtained as a thick brown oil.

1. customVolatiles were then evaporated from the reaction mixture
2. temperaturethe residue was cooled in an ice bath
3. additionIce cold saturated K2CO3 solution (˜200 ml) was slowly added to it
4. extractionThe mixture was extracted with EtOAc (3×250 ml)
5. washCombined organic layers were then washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe crude product was purified on silica column

ORD-Eintrag

ord-335872161edc422ea9969d5103511bba

Quelldatensatz

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08802695B2