Methyl 7-methyl-alpha-oxo-1H-indole-3-acetate → 3-(7-Methyl-1H-indol-3-yl)-4-[2-methyl-5-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-pyrrole-2,5-dione

HRID 1992638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992638
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH2:17][C:18]([NH2:20])=[O:19])[C:11]([N+]([O-])=O)=[N:12][CH:13]=2)[CH2:4][CH2:3]1.C[O:22][C:23](=O)[C:24]([C:26]1[C:34]2[C:29](=[C:30]([CH3:35])[CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)=O.[CH3:37]C([O-])(C)C.[K+]>C1COCC1>[CH3:35][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:29]=1[NH:28][CH:27]=[C:26]2[C:24]1[C:23](=[O:22])[NH:20][C:18](=[O:19])[C:17]=1[C:10]1[C:11]([CH3:37])=[N:12][CH:13]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:9]=1

Komponenten

5

Edukt 3

HCID 11241405Methyl 7-methyl-alpha-oxo-1H-indole-3-acetateHCID 23665647Potassium tert-butoxideHCID 668689562-[5-(4-Methyl-piperazin-1-yl)-2-nitro-pyridin-3-yl]-acetamide

Produkt 1

HCID 668690143-(7-Methyl-1H-indol-3-yl)-4-[2-methyl-5-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-pyrrole-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-[5-(4-Methyl-piperazin-1-yl)-2-nitro-pyridin-3-yl]-acetamide (96 mg, 0.34 mmol) and (7-Methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (127 mg, 0.58 mmol) in dry THF (8.0 mL) is added at 0° C. under an atmosphere of argon, a solution of 1.0 M KOtBu in THF (1.7 ml, 1.7 mmol). After stirring for 2 h at 0° C., TLC analysis indicated complete consumption of the starting materials. The reaction mixture is diluted with EtOAc and washed with brine. The aqueous phase is extracted with EtOAc and the combined organic layers are washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The residue is purified by FCC (EtOAc/AcOH/H2O 6:1:1) to afford the title compound as an orange powder. 1H NMR (d6-DMSO 400 MHz): δ 2.05 (s, 3H), 2.04-2.11 (m, 4H), 2.46 (s, 3H), 3.06-3.14 (m, 4H), 6.35 (d, J=8.1 Hz, 1H), 6.65 (dd, J=8.1, 7.2 Hz, 1H), 6.84 (d, J=7.2 Hz, 1H), 6.87 (d, J=2.0 Hz,1H), 7.95 (s, 1H), 8.16 (d, J=2.0 Hz, 1H). ES+−MS: 447 [M+H]+.

Aufarbeitung

  1. customconsumption of the starting materials
  2. additionThe reaction mixture is diluted with EtOAc
  3. washwashed with brine
  4. extractionThe aqueous phase is extracted with EtOAc
  5. washthe combined organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated at reduced pressure
  8. customThe residue is purified by FCC (EtOAc/AcOH/H2O 6:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-25bd547845e840ee8c32ec2a738f3012
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648989B2

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