Ethylene Glycol → 5-bromo-1-methyl-3-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 879497Notes

Reaction equation

HRID 879497 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([N:17]3[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]3)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 531671-MethylpiperazineHCID 62657Potassium Phosphate, TribasicHCID 598120775-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 867003145-bromo-1-methyl-3-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 5-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.445 mmol), 1-methylpiperazine (356.7 mg, 3.56 mmol), copper(I) iodide (84.8 mg, 0.445 mmol), K3PO4 (378 mg, 1.78 mmol), 1,2-ethanediol (138 mg, 2.225 mmol) in isopropyl alcohol (5 mL) in a sealed tubes was heated at 70° C. for 2 days. After cooling to room temperature, the reaction mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was taken up in EtOAc and the solution was washed with saturated NaHCO3, dried and concentrated. Purification by flash chromatography afforded the title compound. LCMS-ESI+: calc'd for C13H17BrN4 309.1 (M+H+); Found: 309.1 (M+H+).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. washthe solution was washed with saturated NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-6441f764584b43f98fe5d25f8949256d
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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