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

HRID 874522

Reaktionsgleichung

Reaktionsgleichung von HRID 874522
C([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[C:22]([N+:23]([O-])=O)=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=1)=O)(C)(C)C>C(O)(=O)C.[Fe]>[O:5]=[C:6]1[N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]2[N:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][C:22]=2[NH:23]1

Komponenten

4

Edukt 1

HCID 66926258methyl 6-(1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl)-5-nitronicotinate

Produkt 1

HCID 66926220Methyl 6-oxo-5,6-dihydropyrido[2,3-e]pyrrolo[1,2-c]pyrimidine-3-carboxylateAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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, 3 H) 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)+.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated to dryness via rotary evaporation
  3. additionThe resulting residue was diluted with 1:1 DCM
  4. filtrationMeOH (4 mL), filtered
  5. washrinsed with 1:1 DCM
  6. concentrationMeOH (3×2 mL), and the filtrate was then concentrated to dryness via rotary evaporation
  7. filtrationfiltered
  8. washrinsed with H2O (3×2 mL)
  9. customthe resulting solid was dried in vacuo
  10. customThe resulting crude material was purified via medium pressure chromatography
  11. concentrationconcentrated via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-8a2413de0162416b92e54420f48c7377
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980902B2

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