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

HRID 1271387ノート

反応式

HRID 1271387 の反応式
[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

参加物

8

反応物 3

HCID 7912DiisopropylamineHCID 135663-Butyn-1-OLHCID 178448919HCID 178448919、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒2 回HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-814f3d8cfd0c42689fa668e4b24067a3
出典データセット
uspto-grants-2007_04
特許番号
US07205316B2

反応ノート

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