Sodium hydride → HCID 67485570, compound

HRID 1523577Notes

Reaction equation

HRID 1523577 reaction equation
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[H-].[Na+].Br[C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30]>CN(C=O)C.O>[CH2:1]([C:3]1[C:8]([O:9][C:15]2[C:16]([C:19]#[N:20])=[N:17][CH:18]=[C:13]([S:30][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)[CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 24758Sodium hydride2×HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 38372322-ethylpyridin-3-olHCID 178418616HCID 178418616, compound

Product 1

HCID 67485570HCID 67485570, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-ethylpyridin-3-ol (2.5 g, 20.3 mmol) in DMF (20 ml) at 0° C. was added sodium hydride (0.512 g, 21.3 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (4.63 g, 20.3 mmol) was added and the mixture was allowed to warm slowly to ambient temperature and stirred for 2 hours. Pridine-2-thiol (0.804 g, 7.23 mmol) was added followed by sodium hydride (0.182 g, 7.60 mmol) and the mixture was stirred at ambient temperature overnight. Water (200 ml) was added and the mixture was extracted with diethyl ether (3×100 mL), washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified over silica gel (25 to 75% EtOAc in Hexanes) to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (1.4 g, 4.19 mmol).

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. extractionthe mixture was extracted with diethyl ether (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified over silica gel (25 to 75% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-3e235affd4ce4944b0574356f658e632
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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