Cesium fluoride → 5-Aminobiphenyl-2-carbonitrile

HRID 501583

Reaction equation

HRID 501583 reaction equation
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]

Participants

7

Reactant 3

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

Product 1

HCID 441582825-Aminobiphenyl-2-carbonitrileYield 96%

Reagents, catalysts & solvents 3

HCID 178479803HCID 178479803, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-b4b89d34f5d54eef85433dec6ae4d613
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Linked notes

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