2,5-Hexanedione → 1-[3-Bromo-5-(2,5-dimethylpyrrol-1-yl)-4-pyridyl]-4-methyl-piperazine

HRID 524897Notes

Reaction equation

HRID 524897 reaction equation
[Br:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[CH3:16][C:17](=O)[CH2:18][CH2:19][C:20](=O)[CH3:21]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([N:8]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:16])[C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 867209525-Bromo-4-(4-methylpiperazin-1-yl)pyridin-3-amine

Product 1

HCID 867209531-[3-Bromo-5-(2,5-dimethylpyrrol-1-yl)-4-pyridyl]-4-methyl-piperazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-bromo-4-(4-methylpiperazin-1-yl)pyridin-3-amine (3000 mg, 11.06 mmol), hexane-2,5-dione (6.312 g, 6.487 mL, 55.30 mmol) in acetic acid (20 mL) was heated at 70° C. overnight. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and an aqueous saturated solution of NaHCO3. Combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo yielding an oil that was purified by filtration on silica to yield 1-(3-bromo-5-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-4-yl)-4-methylpiperazine as an off-white solid. MS (ES+) 351.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc
  3. extractionCombined organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customyielding an oil that
  8. filtrationwas purified by filtration on silica

Sources & evidence

ORD record
ord-6ca67994b9844a248a37566184c34a58
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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