Ammonium formate → methyl 4H-thieno(3,2-b)pyrrole-2-carboxylate

HRID 1008987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1008987
C([O-])=O.[NH4+].CN(C)/[CH:7]=[CH:8]/[C:9]1[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][C:10]=1[N+:18]([O-])=O>CO.CCOC(C)=O.[Pd]>[S:13]1[C:9]2[CH:8]=[CH:7][NH:18][C:10]=2[CH:11]=[C:12]1[C:14]([O:16][CH3:17])=[O:15]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 12110978methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate

Produkt 1

HCID 12110979methyl 4H-thieno(3,2-b)pyrrole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

10% Pd/C (0.4 eq.) and ammonium formate (6 eq.) were added to a 0.1M solution of methyl 5-[(E)-2-(dimethylamino)ethenyl]-4-nitrothiophene-2-carboxylate in MeOH/EtOAc 1:1, and the mixture was heated to reflux for 30 min; after cooling to RT the flask was flushed with nitrogen a few times, then the reaction mixture was filtered and the solution evaporated i. vac. The residue was dissolved in EtOAc and washed with water and brine, dried over Na2SO4, and concentrated i. vac. The crude product (50% over two steps) was used as such. 1H-NMR (400 MHz, CDCl3, 300 K, δ) 8.44 (bs, 1H), 7.72 (s, 1H), 7.21 (bs, 1H), 6.50 (bs, 1H), 3.91 (s, 3H); MS (ES+) m/z 182 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 min
  3. customwas flushed with nitrogen a few times
  4. filtrationthe reaction mixture was filtered
  5. customthe solution evaporated
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with water and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated i

Quellen und Nachweise

ORD-Eintrag
ord-8d5d77fe4fae4810968e3cdfb86b0e92
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973026B2

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