Pyridine → 2-Amino-5-[1-(4-cyanophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]-6-(2-furyl)nicotinonitrile

HRID 353231Notes

Reaction equation

HRID 353231 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]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[NH:17][CH:16]=2)=[CH:6][C:3]=1[C:4]#[N:5].[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23].N1C=CC=CC=1.CN(C)C=O>O.C([O-])(=O)C.[Cu+2].C([O-])(=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:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([C:27]3[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][CH:26]=3)[CH:16]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 27343264-Cyanophenylboronic acidHCID 99654582-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile

Product 1

HCID 129921402-Amino-5-[1-(4-cyanophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]-6-(2-furyl)nicotinonitrileYield 62%

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 962WaterSolvent

Procedure

2-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile (20 mg, 0.071 mmol), 4-cyanophenylboronic acid (35 mg, 0.24 mmol), copper acetate monohydrate (3.0 mg, 0.015 mmol), pyridine (0.015 mL, 0.19 mmol) and N,N-dimethylformamide (1.0 mL) were introduced into a reaction vessel and stirred at room temperature for 20 hours. Water was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was dried, and then dissolved in dimethyl sulfoxide (1.0 mL) and purified by high performance liquid chromatography, to give the title compound as a yellow solid (8.32 mg, 62%).

Workup

  1. extractionby extracting with ethyl acetate
  2. customThe organic layer was dried
  3. dissolutiondissolved in dimethyl sulfoxide (1.0 mL)
  4. custompurified by high performance liquid chromatography

Sources & evidence

ORD record
ord-7c747ebadead41eba90261d209f3ff9d
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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