Diisopropylamine → 2-(7-Bromo-3-isoquinolinyl)ethanol

HRID 551550

Reaktionsgleichung

Reaktionsgleichung von HRID 551550
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6](/[CH:8]=[N:9]/[C:10]([CH3:13])([CH3:12])C)[CH:7]=1.[CH2:15]([OH:19])CC#C.C(NC(C)C)(C)C>C1(C)C=CC=CC=1.C(Cl)Cl.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:13]=[C:10]([CH2:12][CH2:15][OH:19])[N:9]=[CH:8]2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 3

HCID 7912DiisopropylamineHCID 135663-Butyn-1-OLHCID 178448919HCID 178448919, Verbindung

Produkt 1

HCID 210439272-(7-Bromo-3-isoquinolinyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator2×HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Example 62D (1.3 g, 3.6 mmol), 3-butyn-1-ol (0.3 g, 4.3 mmol), CuI (0.04 g, 0.2 mmol), and PdCl2(PPh3)2 (0.08 g, 0.1 mmol) were combined in toluene (15 mL). The mixture was treated with diisopropylamine (0.54 g, 5.3 mmol) and stirred at room temperature for 4 hours. The mixture was then treated with additional CuI (0.07 g, 0.4 mmol) and heated at 100° C. for 4 hours. The mixture was allowed to cool to room temperature, diluted with 30 mL CH2Cl2, and filtered. The filtrate was washed with 2×10 mL 15% NaCl and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 10:90 MeOH:CHCl3) to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 9.08 (s, 1H), 8.09 (d, J=4 Hz, 1H), 7.73 (dd, J=8, 4 Hz, 1H), 7.63 (d, J=8 Hz, 1H), 7.48 (s, 1H), 4.08 (t, J=4 Hz, 2H), 3.92 (s, 1H), 3.15 (t, J=4 Hz, 2H). 13C NMR (CDCl3, 100 MHz) δ 153.8, 150.3, 134.5, 133.8, 129.4, 127.6, 120.0, 118.6, 62.3, 39.4. MS (DCl/NH3) 252, 254 [M+H]+.

Aufarbeitung

  1. temperatureheated at 100° C. for 4 hours
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washThe filtrate was washed with 2×10 mL 15% NaCl
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, 10:90 MeOH:CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-ee26ee80b319429e988a3d7091080733
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947711B2

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