2-Bromopyridine → HCID 10703742, compound

HRID 1709837Notes

Reaction equation

HRID 1709837 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% ethyl acetate-90% hexanes and 20% ethyl acetate-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% ethyl acetate-90% hexanes and 20% ethyl acetate-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-25c567dc6585427aac6b807367890611
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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