Sodium Carbonate → 3-(Pyridin-3-yl)cyclohex-2-en-1-one

HRID 571964ノート

反応式

HRID 571964 の反応式
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)[CH:10]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 5683453-Chlorocyclohex-2-en-1-oneHCID 27343783-Pyridinylboronic acid

生成物 1

HCID 134025713-(Pyridin-3-yl)cyclohex-2-en-1-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium-DCM complex (313 mg, 0.383 mmol) was added to a stirred mixture of 8a (500 mg, 3.83 mmol), pyridin-3-yl-boronic acid (565 mg, 4.60 mmol) and sodium carbonate (2.87 mL of a 2M aq. solution, 5.74 mmol) in dioxane (14.0 mL) and water (2.00 mL). The resulting mixture was degassed and heated to 95° C. After 7 h, the reaction mixture was cooled to rt, diluted with EtOAc, filtered through a short column of Celite®, eluting copiously with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (0-90% EtOAc/hexanes as eluent) to afford the title compound, 8b. m/z (ES) 174 (MH)+

後処理

  1. customThe resulting mixture was degassed
  2. temperaturethe reaction mixture was cooled to rt
  3. additiondiluted with EtOAc
  4. filtrationfiltered through a short column of Celite®
  5. washeluting copiously with EtOAc
  6. washThe organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by column chromatography on silica gel (0-90% EtOAc/hexanes as eluent)

出典と根拠

ORDレコード
ord-a8cb637dc19e429d8fb295052318e14f
出典データセット
uspto-grants-2015_05
特許番号
US09029377B2

反応ノート

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