2,5-Hexanedione → HCID 11402477, compound

HRID 869158Notes

Reaction equation

HRID 869158 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:8])=[N:6][CH:7]=1.[CH3:9][C:10](=O)[CH2:11][CH2:12][C:13](=O)[CH3:14]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:9])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 80352,5-HexanedioneHCID 6428116-Bromopyridin-3-amine

Product 1

HCID 11402477HCID 11402477, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a 25 mL round bottom flask was added 5-amino-2-bromopyridine (600 mg, 3.5 mmol, 1.0 equiv), hexane-2,5-dione (420 mg, 4.2 mmol, 1.2 equiv), p-toluenesulfonic acid (5 mg), and toluene (3.5 mL). A Dean-Stark trap was fitted on top of the round bottom flask and the reaction mixture was heated to reflux for 2 h. The reaction was then concentrated and purified by silica gel column chromatography (5% ethyl acetate/hexanes) to give 660 mg (76%) of 2-bromo-5-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine.

Workup

  1. customA Dean-Stark trap was fitted on top of the round bottom flask
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2 h
  4. concentrationThe reaction was then concentrated
  5. custompurified by silica gel column chromatography (5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-784646a35a074086a225d894e20bd15c
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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