Potassium Carbonate → 3-(4-Methyl-2-nitro-phenyl)-pyridine

HRID 227235

反応式

HRID 227235 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.[C:21](=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.C([O-])([O-])=O.[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][C:2]1[CH:7]=[CH:6][C:5]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

参加物

9

反応物 3

HCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenolHCID 27343783-Pyridinylboronic acid

生成物 1

HCID 117459723-(4-Methyl-2-nitro-phenyl)-pyridine

試薬・触媒・溶媒 5

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

4-Bromo-2-nitro-phenol (648 mg, 3.0 mmol) and 3-pyridyl boronic acid (387 mg, 3.15 mmol) were diluted with 5 mL of dioxane and placed under N2. Potassium carbonate was diluted in 1 mL of H2O and added to the reaction mixture. Tetrakis(triphenylphosphine) palladium (173 mg, 0.15 mmol) was added, then the reaction was heated to 70° C. and stirred overnight. The reaction was allowed to cool to room temperature, then diluted with 30 mL of EtOAc and 30 mL of 10% Na2CO3. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The material was purified with a Biotage 40M cartridge eluting with hexanes/EtOAc, 1/1 to yield an off white solid.

後処理

  1. additionadded to the reaction mixture
  2. temperatureto cool to room temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe material was purified with a Biotage 40M cartridge
  8. washeluting with hexanes/EtOAc, 1/1
  9. customto yield an off white solid

出典と根拠

ORDレコード
ord-1cd7e63882694d8b92fa652bbf8ab09d
出典データセット
uspto-grants-2009_07
特許番号
US07560462B2

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