2-Bromopyridine → HCID 10703742, compound

HRID 1193661Notes

Reaction equation

HRID 1193661 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:11]#[N:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 24758Sodium hydrideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 10703742HCID 10703742, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of sodium hydride (60%, 1.60 g, 0.04 mole) was washed with dry hexanes. After removal of hexanes a 100 ml portion of dimethyl sulfoxide was added. To this mixture was added a solution of 4-fluorophenylacetonitrile (5.41 g, 0.04 mole). The mixture was stirred 3 hrs at room temperature under nitrogen. 2-Bromopyridine (6.32 g, 0.04 mole) was added to the mixture, the reaction mixture was then stirred overnight at 65° C. The reaction mixture was poured into 1200 ml of water and the aqueous phase was extracted several times with chloroform (the chloroform layer was filtered using Celite). The combined chloroform layer was extracted with water and 5% sodium hydroxide. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give a red oil. The oil was subjected to flash chromatography on silica gel using 10% ethylacetate-90% hexanes and 20% ethylacetate-80% hexanes for elution. Fractions of similar purity was combined and solvent removed in vacuo. The oil obtained was dried in vacuo overnight at 80° C. to give 2.43 g (28.6%) of clear oil.

Workup

  1. customAfter removal of hexanes a 100 ml portion of dimethyl sulfoxide
  2. additionwas added
  3. stirringthe reaction mixture was then stirred overnight at 65° C
  4. extractionthe aqueous phase was extracted several times with chloroform (the chloroform layer
  5. filtrationwas filtered
  6. extractionThe combined chloroform layer was extracted with water and 5% sodium hydroxide
  7. dry with materialThe chloroform layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customsolvent removed
  10. customto give a red oil
  11. washThe oil was subjected to flash chromatography on silica gel using 10% ethylacetate-90% hexanes and 20% ethylacetate-80% hexanes for elution
  12. customsolvent removed in vacuo
  13. customThe oil obtained
  14. customwas dried in vacuo overnight at 80° C.

Sources & evidence

ORD record
ord-593e30d33511448184404adbc43a8d0a
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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