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

HRID 1014187ノート

反応式

HRID 1014187 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-49ca80bb5a7b44b887e485767bcee573
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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