Cesium fluoride → 5-Aminobiphenyl-2-carbonitrile

HRID 501583

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HRID 501583 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

HCID 441582825-Aminobiphenyl-2-carbonitrile수율 96%

시약·촉매·용매 3

HCID 178479803HCID 178479803, 화합물촉매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b4b89d34f5d54eef85433dec6ae4d613
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772267B2

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