Potassium Carbonate → 2-Amino-5-(4-cyanophenyl)-6-(2-furyl)nicotinonitrile

HRID 353227Notes

Reaction equation

HRID 353227 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].[C:16]([C:18]1[CH:23]=[CH:22][C:21](OB(O)O)=[CH:20][CH:19]=1)#[N:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7]([C:21]2[CH:22]=[CH:23][C:18]([C:16]#[N:17])=[CH:19][CH:20]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 129921342-Amino-5-bromo-6-(2-furyl)nicotinonitrileHCID 220496434-Cyanophenylboric acid

Product 1

HCID 129921362-Amino-5-(4-cyanophenyl)-6-(2-furyl)nicotinonitrileYield 15.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-bromo-6-(2-furyl)nicotinonitrile (20 mg, 75.7 μmol), 4-cyanophenylboric acid (30 mg, 204 μmol), dichlorobis(acetonitrile) palladium (II) (2 mg, 7.71 μmol), and a solution of 2 M aqueous potassium carbonate (150 μL, 300 μmol) in N,N-dimethylformamide (0.6 mL) was stirred at 80° C. for 14 hours. After cooling as it was, the reaction solution was diluted with ethyl acetate and water. After filtering off the insoluble matters, the organic layer in the filtrate was concentrated. A half of the residue was purified by HPLC on a reverse phase column and using a water-acetonitrile-trifluoroacetic acid system as the elution solvent, to give the title compound (3.33 mg).

Workup

  1. temperatureAfter cooling as it
  2. filtrationAfter filtering off the insoluble matters
  3. concentrationthe organic layer in the filtrate was concentrated
  4. customA half of the residue was purified by HPLC on a reverse phase column

Sources & evidence

ORD record
ord-fcf0088410984b72aa6adb4ef9017273
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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