Sodium ethoxide → 6-Amino-4-furan-2-yl-2-(2-pyridin-2-yl-ethylsulfanyl)-nicotinonitrile

HRID 1356047Notes

Reaction equation

HRID 1356047 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[S:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.CC[O-].[Na+].Br.Br[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>C(O)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:5]([C:9]#[N:10])=[C:6]([S:8][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:7]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 129138592-(2-Bromoethyl)pyridine hydrobromideHCID 185073536-Amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile

Product 1

HCID 185075506-Amino-4-furan-2-yl-2-(2-pyridin-2-yl-ethylsulfanyl)-nicotinonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 100 mg (0.46 mmol) 6-amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile in 3.4 ml ethanol were added 0.60 ml (1.60 mmol) sodium ethylate solution (2.67M in ethanol) and 368 mg (1,38 mmol) 2-(2-bromoethyl)pyridine hydrobromide and the reaction mixture heated at reflux for 1 hour. The reaction mixture was then concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether to afford 112 mg (76%) 6-amino-4-furan-2-yl-2-(2-pyridin-2-yl-ethylsulfanyl)-nicotinonitrile as a white crystalline solid. ES-MS m/e (%): 323 (M+H+, 100).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-e69670d839b94042b3aca8b0e2bda29f
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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