Acetic Acid → 2-(4-Methoxyquinolin-6-yl)-1-(6-methylpyridin-2-yl)ethanone

HRID 968291

반응식

HRID 968291 반응식
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:12][CH3:13].CC(C)([O-])C.[K+].[CH3:20][C:21]1[N:26]=[C:25]([C:27](=[O:29])[CH3:28])[CH:24]=[CH:23][CH:22]=1.C(O)(=O)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>[CH3:13][O:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH2:28][C:27]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:20])[N:26]=3)=[O:29])[CH:3]=2)[N:8]=[CH:7][CH:6]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 1388722-Acetyl-6-methylpyridineHCID 222886546-Chloro-4-methoxyquinolineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 222886552-(4-Methoxyquinolin-6-yl)-1-(6-methylpyridin-2-yl)ethanone수율 56%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl촉매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

To a 20 mL threaded pressure tube was added 6-Chloro-4-methoxy-quinoline (298 mg, 1.54 mmol), palladium (II) acetate (7 mg, 0.03 mmol), 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (a.k.a. AMPHOS, 24 mg, 0.06 mmol), and potassium tert-butoxide (1M in TH, 3.7 mmol). This mixture was stirred and 1-(6-Methyl-pyridin-2-yl)-ethanone was added. The pressure tube was then sealed and heated to 70° C. The reaction mixture was stirred at 70° C. for 18 hours. LC-MS showed product. The reaction mixture was then cooled and poured into a solution of 600 μL of glacial acetic acid in 30 mL of water. Title compound was extracted with 3×30 mL of chloroform. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated via rotary evaporator. The residue was purified by flash column chromatography (silica gel) using a 1% Methanol /Chloroform solvent system affording 255 mg of desired product (56% yield). HPLC=4.39 min, LC-MS=293 (M+H, mw=292.34).

후처리

  1. customThe pressure tube was then sealed
  2. stirringThe reaction mixture was stirred at 70° C. for 18 hours
  3. temperatureThe reaction mixture was then cooled
  4. extractionTitle compound was extracted with 3×30 mL of chloroform
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated via rotary evaporator
  8. customThe residue was purified by flash column chromatography (silica gel)

출처 및 근거

ORD 기록
ord-be9f08471873469c8098d3f698331953
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958354B2

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