1,10-Phenanthroline → HCID 67089033, compound

HRID 1943928Notes

Reaction equation

HRID 1943928 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[F-].[K+].[CH3:39][O:40][CH2:41][CH2:42][OH:43]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cu]I>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:4]2[C:5]3=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[C:10]3[C:2]([O:43][CH2:42][CH2:41][O:40][CH3:39])=[N:3]2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 80192-MethoxyethanolHCID 522689Potassium FluorideHCID 67088863HCID 67088863, compound

Product 1

HCID 67089033HCID 67089033, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Iodo-1-(4-methoxybenzyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (2.0 g, 4.88 mmol), 1,10-phenanthroline (0.879 g, 4.88 mmol), copper (I) iodide (0.929 g, 4.88 mmol), potassium fluoride (4.96 g, 34.1 mmol), and 2-methoxyethanol (11.1 g, 146 mmol) were suspended in toluene (65 mL) and stirred at reflux for 20 hours. The mixture was cooled, diluted with EtOAc, filtered through a plug of silica, and concentrated. The crude product was purified via column chromatography eluting with 6:4 EtOAc-hexanes to afford 1-(4-methoxybenzyl)-3-(2-methoxyethoxy)-5-nitro-1H-pyrazolo[3,4-b]pyridine (400 mg, 1.12 mmol, 22.9%).

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated
  5. customThe crude product was purified via column chromatography
  6. washeluting with 6:4 EtOAc-hexanes

Sources & evidence

ORD record
ord-7aa79b01c32f46d482cc5ec32cdfa9cf
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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