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

HRID 1271387Notes

Reaction equation

HRID 1271387 reaction equation
[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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 15D (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]+.

Workup

  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)

Sources & evidence

ORD record
ord-814f3d8cfd0c42689fa668e4b24067a3
Source dataset
uspto-grants-2007_04
Patent number
US07205316B2

Reaction notes

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