Potassium Carbonate → HCID 67528343、化合物

HRID 1867548ノート

反応式

HRID 1867548 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)#[N:12].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[OH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:11]#[N:12])[CH:18]=2)=[CH:3][CH:4]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 728512-(4-Bromophenyl)ethanolHCID 27343253-Cyanophenylboronic acid

生成物 1

HCID 67528343HCID 67528343、化合物収率 87.1%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

A mixture of 3 g (14.92 mmol) of 2-(4-bromophenyl)ethanol, 2.85 g (19.40 mmol) of 3-cyanophenylboronic acid, 5.15 g (37.30 mmol) of potassium carbonate, 4.81 g (14.92 mmol) of tetran-butylammonium bromide and 0.067 g (0.30 mmol) of palladium diacetate in 15 ml of water is heated at 100° C. under an argon atmosphere overnight. It is cooled to ambient temperature, diluted with water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and evaporated. It is subsequently purified by chromatography on silica gel, eluting with a 70/30 then 50/50 mixture of cyclohexane and ethyl acetate, to give 2.90 g of product in the form of an oil, which is used as it is in the following step.

後処理

  1. temperatureIt is cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customevaporated
  5. customIt is subsequently purified by chromatography on silica gel
  6. washeluting with a 70/30
  7. addition50/50 mixture of cyclohexane and ethyl acetate

出典と根拠

ORDレコード
ord-1f7465575227425e989c725bbea15770
出典データセット
uspto-grants-2009_12
特許番号
US07632850B2

反応ノート

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