Toluene → 2-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine

HRID 1978037Notes

Reaction equation

HRID 1978037 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1(C)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(CC(=O)C)C(C)=O.C(OCC)(=O)C.CCCCCC>C(O)(=O)C.C(OCC)(=O)C>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:1]2[C:11]([CH3:12])=[CH:10][CH:9]=[C:14]2[CH3:13])[N:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 80352,5-HexanedioneHCID 3008092-Amino-6-bromopyridineHCID 21226206Ethyl acetate hexane

Product 1

HCID 155127672-Bromo-6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridineYield 47%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 1 L round-bottomed flask equipped with Dean-Stark trap, condenser, and nitrogen inlet were added 21.3 g(123 mmol) 2-amino-6-bromopyridine, 400 mL toluene, 14.1 g(123 mmol) acetonylacetone, and 20 drops acetic acid. The reaction was refluxed 5 days (tlc in 1/1:ethyl acetate/hexane, Rf=0.8 (product), 0.5 (starting material)), cooled, poured into ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 5% methanol in methylene chloride to afford 14.4 g(47%) of the product as a low-melting yellow solid.

Workup

  1. customTo a 1 L round-bottomed flask equipped with Dean-Stark trap, condenser, and nitrogen inlet
  2. temperaturecooled
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-9c61cf5e34ea402e898575236a6c25f3
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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