methyl 6-(1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl)-5-nitronicotinate → Methyl 6-oxo-5,6-dihydropyrido[2,3-e]pyrrolo[1,2-c]pyrimidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 6-(1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl)-5-nitronicotinate (0.0672 g, 0.193 mmol) in Acetic Acid (Volume: 1.5 mL) was added IRON (0.054 g, 0.967 mmol) at 23° C. The reaction was stirred at 80° C. for 6 hr. The reaction mixture was then cooled to room temperature and concentrated to dryness via rotary evaporation. The resulting residue was diluted with 1:1 DCM:MeOH (4 mL), filtered, rinsed with 1:1 DCM:MeOH (3×2 mL), and the filtrate was then concentrated to dryness via rotary evaporation. The residue was re-suspended in H2O (4 mL), filtered, rinsed with H2O (3×2 mL), and the resulting solid was dried in vacuo. The resulting crude material was purified via medium pressure chromatography using a gradient eluant of CH2Cl2/MeOH. The appropriate fractions were combined and concentrated via rotary evaporation to provide methyl 6-oxo-5,6-dihydropyrido[2,3-e]pyrrolo[1,2-c]pyrimidine-3-carboxylate (0.0294 g, 0.121 mmol, 62.5% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.91 (s, 3H) 6.82 (dd, J=3.54, 3.03 Hz, 1 H) 7.26 (dd, J=3.54, 1.52 Hz, 1 H) 7.80 (dd, J=3.03, 1.52 Hz, 1 H) 8.07 (d, J=2.02 Hz, 1 H) 8.88 (d, J=1.77 Hz, 1 H) 11.84 (s, 1 H). ESI-MS: m/z 244.1 (M+H)+.

Provenance & Evidence