Potassium Phosphate, Tribasic → Methyl 3-(3-pyridinyl)benzoate

HRID 489858ノート

反応式

HRID 489858 の反応式
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.[Pd]>[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:16]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 69258Methyl 3-iodobenzoateHCID 6428513-(Diethylboryl)pyridine

生成物 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoate収率 68.1%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of diethyl(3-pyridyl)borane (176.4 g, 1.2 mole), methyl-3-iodobenzoate (262 g, 1 mole), potassium phosphate (318.4 g, 1.5 mole) and tetrakistriphenlyphosphine palladium (0) (57.8 g, 0.05 mole) in DMF (1000 ml) was heated at 80 degrees under argon. After 10 h, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was filtered and washed with water. To the organic fraction was added concentrated HCL (65 ml). The organic layer was separated and extracted with aqueous HCl. The combined acid extractions were treated with ethyl acetate, followed by 50% aqueous sodium hydroxide (55 ml). The organic layer was separated, washed with water and saturated sodium bicarbonate solution, then dried over sodium sulfate. The solution was filtered and concentrated to give methyl-3-(pyridin-3-yl)benzoate (145.3 g).

後処理

  1. temperaturewas heated at 80 degrees under argon
  2. extractionextracted with ethyl acetate
  3. filtrationThe organic layer was filtered
  4. washwashed with water
  5. additionTo the organic fraction was added
  6. concentrationconcentrated HCL (65 ml)
  7. customThe organic layer was separated
  8. extractionextracted with aqueous HCl
  9. extractionThe combined acid extractions
  10. additionwere treated with ethyl acetate
  11. customThe organic layer was separated
  12. washwashed with water and saturated sodium bicarbonate solution
  13. dry with materialdried over sodium sulfate
  14. filtrationThe solution was filtered
  15. concentrationconcentrated

出典と根拠

ORDレコード
ord-eba2f6dfc8da4254ba461b6997d1bf30
出典データセット
uspto-grants-2005_12
特許番号
US06979693B2

反応ノート

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