Water → HCID 67487618, compound

HRID 1511068Notes

Reaction equation

HRID 1511068 reaction equation
[CH3:1][C:2]1[C:3](=[S:8])[NH:4][CH:5]=[CH:6][CH:7]=1.Br[C:10]1[CH:11]=[C:12]([O:18][C:19]2[C:20]([CH3:25])=[N:21][CH:22]=[CH:23][CH:24]=2)[C:13]([C:16]#[N:17])=[N:14][CH:15]=1.[H-].[Na+].O>CN(C=O)C>[CH3:1][C:2]1[C:3]([S:8][C:10]2[CH:11]=[C:12]([O:18][C:19]3[C:20]([CH3:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13]([C:16]#[N:17])=[N:14][CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 53714503-Methyl-2(1H)-pyridinethioneHCID 67485726HCID 67485726, compound

Product 1

HCID 67487618HCID 67487618, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-Methylpyridine-2(1H)-thione (0.906 g, 7.24 mmol) and 5-bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (2.00 g, 6.89 mmol) were dissolved in DMF (12 mL) and the mixture was cooled to 0° C. Sodium hydride (95%; 0.183 g, 7.24 mmol) was slowly added and the reaction was warmed to ambient temperature and stirred overnight. The reaction mixture was poured into water (100 mL), stirred for 30 minutes, then filtered to afford a solid which was purified over silica gel (2:3 hexanes:ethyl acetate). Concentration of the second UV active fraction to elute afforded 5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)picolinonitrile (1.40 g, 4.19 mmol, 60.7% yield) as a pale yellow/off white powder/crystals.

Workup

  1. temperaturethe reaction was warmed to ambient temperature
  2. stirringstirred for 30 minutes
  3. filtrationfiltered
  4. customto afford a solid which
  5. customwas purified over silica gel (2:3 hexanes:ethyl acetate)
  6. washConcentration of the second UV active fraction to elute

Sources & evidence

ORD record
ord-2f5ffc3fc6994591bc480ffbc62668f2
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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