Triphenyl phosphite → HCID 58324498, Verbindung

HRID 716377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716377
C[O:2][C:3]([C:5]1[N:6]([C:10]2[C:19]([N+:20]([O-])=O)=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)=O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[O:2]=[C:3]1[NH:20][C:19]2[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[N:11][C:10]=2[N:6]2[CH:7]=[CH:8][CH:9]=[C:5]12

Komponenten

6

Edukt 2

HCID 7540Triphenyl phosphiteHCID 58324515methyl 6-(2-(methoxycarbonyl)-1H-pyrrol-1-yl)-5-nitronicotinate

Produkt 1

HCID 58324498HCID 58324498, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 516859Ammonium metavanadateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl 6-(2-(methoxycarbonyl)-1H-pyrrol-1-yl)-5-nitronicotinate (5.00 g, 16.38 mmol) was dissolved in dichloromethane (Volume: 82 ml) and to this solution was added triphenyl phosphite (0.051 g, 0.164 mmol), ammonium metavanadate (0.115 g, 0.983 mmol) and Pt/C (5% wt.) (0.639 g, 0.164 mmol). The reaction mixture was hydrogenated at 100 psi at 25° C. for 36 h. The reaction mixture was filtered through a short plug of celite and the plug and precipitate were washed well with methanol (100 mL) and then MeOH:DCM (100 mL, 1:1). The solids (celite and Pt/C) were continuously extracted with MeOH/DCM mixture (1:1) in a Soxlet extractor for 2 d. The extracts were combined with the earlier filtrates, concentrated in vacuo, crystallized with MeOH (100 mL) and the resulting solid was filtered off and suspended in ethyl ether (200 mL). The solid were filtered off and dried in vacuum to afford methyl 6-oxo-5,6-dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine-3-carboxylate (2.15 g, 8.84 mmol, 54.0% yield) as a grey solid. 1H NMR (DMSO-d6) δ 11.49 (s, 1H), 8.69 (s, 1H), 8.15 (br. s., 1H), 8.11 (s, 1H), 7.16 (d, J=2.5 Hz, 1H), 6.78 (t, J=3.0 Hz, 1H), 3.91 (s, 3H). [M+H] calc'd for C12H9N3O3, 244. found, 244.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a short plug of celite
  2. washthe plug and precipitate were washed well with methanol (100 mL)
  3. extractionThe solids (celite and Pt/C) were continuously extracted with MeOH/DCM mixture (1:1) in a Soxlet extractor for 2 d
  4. concentrationconcentrated in vacuo
  5. customcrystallized with MeOH (100 mL)
  6. filtrationthe resulting solid was filtered off
  7. filtrationThe solid were filtered off
  8. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cb79a3d4939346499ae85c6d76b53849
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187497B2

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