Sodium Carbonate → 4-(3-Methoxy-4-nitrophenyl)pyridine

HRID 1014187노트

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HRID 1014187 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 811105-Chloro-2-nitroanisoleHCID 27343783-Pyridinylboronic acid

생성물 1

HCID 137288334-(3-Methoxy-4-nitrophenyl)pyridine수율 65,813.398%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

Nitrogen was bubbled through dioxane (800 mL) for 1 h followed by the addition of 4-chloro-2-(methyloxy)-1-nitrobenzene (61 g, 0.33 mol), 3-pyridinylboronic acid (Boron Molecular, 40 g, 0.33 mmol), dichloro(triphenylphosphine)palladium (10 g, 14 mmol), and degassed aqueous 3 N Na2CO3 (325 mL, 975 mmol). The reaction mixture was stirred with a mechanical stirrer and heated at 90° C. for 3 h. The reaction was cooled and most of the dioxane was removed in vacuo. It was diluted with water and then extracted with Ethyl acetate. Combined organic phases were dried (Mg2SO4), filtered and concentrated. The resultant solid was washed with diethyl ether to afford 4-(3-methoxy-4-nitrophenyl)pyridine (50 g, 66% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.05 (s, 3 H), 7.53 (dd, J=8.4, 1.8 Hz, 1 H), 7.69 (d, J=1.8 Hz, 1 H), 7.84 (d, J=6.2 Hz, 2 H), 8.02 (d, J=8.4 Hz, 1 H), 8.72 (d, J=6.2 Hz, 2 H). ESIMS (M+H)+=231.

후처리

  1. customNitrogen was bubbled through dioxane (800 mL) for 1 h
  2. customwas removed in vacuo
  3. additionIt was diluted with water
  4. extractionextracted with Ethyl acetate
  5. dry with materialCombined organic phases were dried (Mg2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe resultant solid was washed with diethyl ether

출처 및 근거

ORD 기록
ord-49ca80bb5a7b44b887e485767bcee573
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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