Cesium fluoride → 5-Aminobiphenyl-2-carbonitrile

HRID 501583

反応式

HRID 501583 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]#[N:10])[NH2:5].[F-].[Cs+].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1C(=O)CCC1.CCOC(C)=O.Cl[Pd](Cl)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)P(C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:9]([C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:10]

参加物

7

反応物 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 887284-Amino-2-chlorobenzonitrile

生成物 1

HCID 441582825-Aminobiphenyl-2-carbonitrile収率 96%

試薬・触媒・溶媒 3

HCID 178479803HCID 178479803、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

Commercially available 3-chloro-4-cyanoaniline (305 mg, 2.0 mmol) was dissolved in NMP (8 mL), and CsF (608 mg, 4.0 mmol), phenyl boronic acid (268 mg, 2.2 mmol) and dichlorobis(tricyclohexylphosphino)palladium (73 mg, 0.1 mmol) were added. The reaction was then heated to 100° C. for 16 h. After cooling to rt, the reaction mixture was taken up in EtOAc, washed with water (2×), dried (Na2SO4), concentrated under reduced pressure, and purified by silica gel flash chromatography eluting with EtOAc/hexanes (1:1) to give compound 47A (371 mg, 96%) as a yellow solid. LC/MS m/z 195 [M+H]+.

後処理

  1. temperatureAfter cooling to rt
  2. washwashed with water (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel flash chromatography
  6. washeluting with EtOAc/hexanes (1:1)

出典と根拠

ORDレコード
ord-b4b89d34f5d54eef85433dec6ae4d613
出典データセット
uspto-grants-2010_08
特許番号
US07772267B2

関連ノート

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