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

HRID 8216

反応式

HRID 8216 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 219926374-(2-(2-Pyridyl)ethynyl)quinoline収率 43.4%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6a89cb4b4dfe40218f7f1ec5cf9e62e9
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

関連ノート

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