Potassium Carbonate → 2-Phenylpyridine

HRID 2093729노트

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HRID 2093729 반응식
Cl[C:2]1[C:7](CCC(O)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866427913-(2-chloropyridin-3-yl)propanoic acid

생성물 1

HCID 138872-Phenylpyridine수율 91%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Pd(PPh3)4 (3.0 g, 2.6 mmol) was added to a solution of 2-chloro-3-carboxyethylpyridine (25 g, 134.7 mmol), phenylboronic acid (21.04 g, 172.6 mmol) and K2CO3 (55.1 g, 399 mmol) in 1,4-dioxane (200 mL) and water (200 mL). The reaction mixture was heated at 100° C. for 2 h. The solution was then cooled to room temperature and the dioxane was removed under reduced pressure. The resulting aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried (Na2SO4), filtered through celite, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes) to get the 2-phenylpyridine derivative in 91% yield (27.98 g). LC-MS Rt (retention time): 2.45 min, MS: (ES) m/z 228 (M+H+).

후처리

  1. temperatureThe solution was then cooled to room temperature
  2. customthe dioxane was removed under reduced pressure
  3. extractionThe resulting aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered through celite
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-d354aa115136433eac79552d83822487
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445515B2

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