Water → 3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(5-1-naphthyl-1H-indol-3-yl)pyrrole-2,5-dione

HRID 63554

Reaktionsgleichung

Reaktionsgleichung von HRID 63554
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:14]1([C:26]2[C:27](=[O:42])[NH:28][C:29](=[O:41])[C:30]=2[C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37](Br)[CH:38]=3)[NH:33][CH:32]=2)[C:24]2=[C:25]3[C:20](=[CH:21][CH:22]=[CH:23]2)[CH2:19][CH2:18][CH2:17][N:16]3[CH:15]=1.O>C1(C)C=CC=CC=1.C(O)C.C([O-])(O)=O.[Na+]>[C:14]1([C:26]2[C:27](=[O:42])[NH:28][C:29](=[O:41])[C:30]=2[C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[CH:38]=3)[NH:33][CH:32]=2)[C:24]2=[C:25]3[C:20](=[CH:21][CH:22]=[CH:23]2)[CH2:19][CH2:18][CH2:17][N:16]3[CH:15]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 2545321-Naphthaleneboronic acidHCID 225568693-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(5-bromo-1H-indol-3-yl)-pyrrole-2,5-dione

Produkt 1

HCID 670170493-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(5-1-naphthyl-1H-indol-3-yl)pyrrole-2,5-dioneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1-naphthyl boronic acid (41 mg, 0.24 mmol), 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1yl)-4-(5-bromo-1H-indol-3-yl)pyrrole-2,5-dione (88 mg, 0.2 mmol) (prepared as in Example 24), tetrakistriphenylphosphine palladium (5 mol %) in toluene (4 ml), ethanol (4 ml), saturated NaHCO3 (1 ml), and water (2 ml) was heated at 100° C. under nitrogen for 5 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate (3×15 ml) and concentrated. The residue was purified by silica gel chromatography, eluting with ethyl acetate/hexanes (1:4) to afford 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(5-1-naphthyl-1H-indol-3-yl)pyrrole-2,5-dione as a bright red solid (70 mg, 71%). 1H NMR (CD3OD) δ: 1.80-1.92 (m, 2H), 2.72-2.80 (t, J=6.0 Hz, 2H), 3.94-3.99 (t, J=6.0 Hz, 2H), 6.50-6.58 (m, 3H), 6.66 (s, 1H), 6.72 (m, 1H), 6.98 (dd, J=8.4 Hz, J′=2.0 Hz, 1H), 7.00-7.50 (m, 2H), 7.28 (dd, J=6.8 Hz, J′=8.4 Hz, 1H), 7.38-7.43 (m, 2H), 7.61 (s, 1H), 7.72 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.97 (s, 1H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×15 ml)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with ethyl acetate/hexanes (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-9641a976870947e89261d79992fa3dd9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447088B2

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