Triethylamine → 4-(2-(2-Pyridyl)ethynyl)quinoline

HRID 8216

반응식

HRID 8216 반응식
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42](=O)[CH2:43][C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=[CH:46][CH:45]=1.C(N(CC)CC)C>ClCCCl>[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42]#[C:43][C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=[CH:46][CH:45]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 109338561-(Pyridin-2-yl)-2-(quinolin-4-yl)ethanone

생성물 1

HCID 219926374-(2-(2-Pyridyl)ethynyl)quinoline수율 43.4%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

A mixture of triphenyphosphine oxide (5.56 g, 10 mmol) in 1,2-dichloroethane (30 mL) is cooled in an ice bath. Trifluoromethanesulfonic anhydride (1.57 mL, 10 mmol) is added dropwise over 15 min. To this mixture is added a solution of 1-(2-pyridyl)-2-(4-quinolyl)ethan-1-one (2.5 g, 10 mmol) in 1,2-dichloroethane (10 mL) and triethylamine (2.84 mL, 20 mmol). The ice bath is removed and the mixture heated at reflux for 16 h. The mixture is diluted with dichloromethane (100 mL) and washed with water (3×100 mL), dried (magnesium sulfate), filtered, concentrated in vacuo, and chromatographed on SiO2 (0 to 100% hexane in ethyl acetate) to yield 1 g of title compound as an oil.

후처리

  1. temperatureis cooled in an ice bath
  2. customThe ice bath is removed
  3. temperaturethe mixture heated
  4. temperatureat reflux for 16 h
  5. additionThe mixture is diluted with dichloromethane (100 mL)
  6. washwashed with water (3×100 mL)
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customchromatographed on SiO2 (0 to 100% hexane in ethyl acetate)

출처 및 근거

ORD 기록
ord-6a89cb4b4dfe40218f7f1ec5cf9e62e9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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