Cesium fluoride → 5-Aminobiphenyl-2-carbonitrile

HRID 751099

반응식

HRID 751099 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

반응 조건

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 (73mg, 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 pressue, 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 pressue
  5. custompurified by silica gel flash chromatography
  6. washeluting with EtOAc/hexanes (1:1)

출처 및 근거

ORD 기록
ord-a89eded3fe944538b91a7c4330a9b33f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405234B2

연결된 노트

불러오는 중…