Ethylene Oxide → 4-[7-(2-Hydroxyethyl)-3-isoquinolinyl]benzonitrile

HRID 273233

반응식

HRID 273233 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[CH2:25]1[O:27][CH2:26]1>C1COCC1>[OH:27][CH2:26][CH2:25][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6354Ethylene OxideHCID 671042584-(7-Bromo-3-isoquinolinyl)benzonitrileHCID 178418339Butyllithium

생성물 1

HCID 671046674-[7-(2-Hydroxyethyl)-3-isoquinolinyl]benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-60 °C

실험 절차

The product from Example 74A (4 mmol) is dissolved in 20 mL THF and is cooled to −60° C. under nitrogen. n-BuLi (4.4 mmol) is added dropwise, and the mixture is stirred at −60° C. for additional 30 minutes. A solution of ethylene oxide (20 mmol) in 10 ml THF is added and the mixture is allowed to warm to 10° C. and is stirred to complete the reaction. The mixture iss cooled back down to 0° C. and is slowly quenched with 2N HCl to pH=3. The solvent is removed under vacuum and the residue is dissolved in 20 mL methylene chloride, is washed with water, and is concentrated under reduced pressure. The residue is chromatographed on silica gel (5:95 MeOH:CHCl3) to provide the title compound.

후처리

  1. temperatureto warm to 10° C.
  2. stirringis stirred
  3. customthe reaction
  4. temperatureThe mixture iss cooled back down to 0° C.
  5. customis slowly quenched with 2N HCl to pH=3
  6. customThe solvent is removed under vacuum
  7. dissolutionthe residue is dissolved in 20 mL methylene chloride
  8. washis washed with water
  9. concentrationis concentrated under reduced pressure
  10. customThe residue is chromatographed on silica gel (5:95 MeOH:CHCl3)

출처 및 근거

ORD 기록
ord-c6b33ab4fbfa4fa5a4c55b56fb70c48d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456196B2

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