Ethyl 2-(7-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate → ethyl 2-(7-methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 1964150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964150
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][C:14](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]3=[CH:6][C:5]=2[C:4]=1[CH3:21]>CCOC(C)=O.C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]3=[CH:6][C:5]=2[C:4]=1[CH3:21]

Komponenten

5

Edukt 1

HCID 67249397Ethyl 2-(7-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate

Produkt 1

HCID 67249023ethyl 2-(7-methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 2-(7-methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate (351 mg, 1.23 mmol) was dissolved in EtOAc (6 mL) and ethanol (6 mL), 10% Palladium on carbon (120 mg) was added. The reaction was degassed and charged with hydrogen, then stirred at room temperature overnight. The solid was filtered off. The filtrate was concentrated to give the title compound (320 mg) as an oil without further purification. LCMS m/z=288.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (t, J=7.1 Hz, 3H), 2.25-2.32 (m, 1H), 2.40 (s, 3H), 2.58 (dd, J=16.0 and 8.6 Hz, 1H), 2.80-2.95 (m, 2H), 3.73-3.80 (m, 1H), 3.85 (s, 3H), 3.95-4.02 (m, 1H), 4.06-4.18 (m, 1H), 4.18-4.26 (m, 2H), 6.11 (s, 1H), 6.84 (d, J=8.6 Hz, 1H), 7.02 (d, J=8.6 Hz, 1H).

Aufarbeitung

  1. customThe reaction was degassed
  2. additioncharged with hydrogen
  3. filtrationThe solid was filtered off
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e53861bff3474d58946e696eab6526d1
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415484B2

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