HCID 12260467, compound → HCID 71087757, compound

Participants

Reaction Steps

In a 500 ml round bottom flask, methyl 3-(dimethylamino)-2-((dimethylamino)methyleneamino)acrylate (1A, 12 g, 61 mmol) was dissolved in acetic acid (45 ml) and TFA (15 ml). 1-Ethyl-3-methyl-1H-pyrrole (6.7 g, 61 mmol) was added and the mixture was stirred at room temperature for an hour and then at 110° C. for 4 hours. Volatiles were then evaporated from the reaction mixture, the residue was cooled in an ice bath and 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 a silica column using hexane-EtOAc (0-100%). Pure fractions were combined and evaporated to give the product methyl 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1N, 6.1 g, 46% yield). 1H NMR (400 MHz, DMSO-d6) d ppm 1.34 (t, J=7.20 Hz, 3 H) 2.34 (d, J=1.01 Hz, 3 H) 3.88 (s, 3 H) 4.26 (q, J=7.24 Hz, 2 H) 7.48 (d, J=1.01 Hz, 1 H) 8.20 (d, J=1.01 Hz, 1 H) 8.85 (d, J=1.01 Hz, 1 H).

Provenance & Evidence