Tetrahydrofuran → 3-(4-Methoxy-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione

HRID 2215770

Reaktionsgleichung

Reaktionsgleichung von HRID 2215770
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([NH2:14])=[O:13])[CH:4]=[CH:3]1.C[O:16][C:17](=O)[C:18]([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[O:29][CH3:30])[NH:22][CH:21]=1)=O.CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[CH3:30][O:29][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:28]=1[C:20]([C:18]1[C:17](=[O:16])[NH:14][C:12](=[O:13])[C:11]=1[C:9]1[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=1[N:2]([CH3:1])[CH:3]=[CH:4]3)=[CH:21][NH:22]2

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 114353972-(1-methyl-1H-indol-7-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 53419524Methyl 2-(4-Methoxy-3-indolyl)-2-oxoacetate

Produkt 1

HCID 219500313-(4-Methoxy-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dioneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-(1-methyl-1H-indol-7-yl)-acetamide (0.539 g, 2.87 mmol) and (4-methoxy-1H-indol-3-yl)-oxo-acetic acid methyl ester (0.656 g, 2.81 mmol) in DMF (40 mL) under N2 was added a 1.0 M solution of potassium-tert-butoxide in THF (10 mL, 10 mmol) dropwise over 5 minutes. The mixture was heated at 60° C. for 15 h, quenched with 1N HCl (excess) and poured into EtOAc. The organic layer was separated, washed with water (3×), saturated aq NaHCO3, and brine, dried (MgSO4), filtered and concentrated onto flash SiO2. Flash chromatography (30–40% hexane/EtOAc) gave the title compound (0.414 g, 40%) as a red solid, which was dried under vacuum overnight. 1H NMR (400 MHz, DMSO-d6) 11.49 (br s, 1H), 11.08 (s, 1H), 7.49 (dd, J=7, 3 Hz, 1H), 7.30 (d, J=3 Hz, 1H), 7.25 (d, J=3 Hz, 1H), 6.86–7.05 (m 4H), 6.39 (d, J=7 Hz, 1H), 6.42 (d, J=3 Hz, 1H), 3.76 (s, 3H), 3.34 (s, 3H). MS (electrospray, m/z) 372.1 (M++1), 370 (M−−1). HRMS 372.1347 (M++1, calcd for C22H18N3O3 372.1348).

Aufarbeitung

  1. customquenched with 1N HCl (excess)
  2. additionpoured into EtOAc
  3. customThe organic layer was separated
  4. washwashed with water (3×), saturated aq NaHCO3, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated onto flash SiO2

Quellen und Nachweise

ORD-Eintrag
ord-cec2aa082d7a45b986a677801a9ce07c
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109229B2

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