Ethanol → HCID 67088924, compound

HRID 1943933Notes

Reaction equation

HRID 1943933 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-])=O)[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.CCO.[NH4+].[Cl-]>[Fe].O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH2:11])[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

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 67088863HCID 67088863, compound

Product 1

HCID 67088924HCID 67088924, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-Iodo-1-(4-methoxybenzyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (3.5 g, 8.5 mmol), EtOH (70 mL), water (30 mL), Fe (0) (1.9 g, 34 mmol), and NH4Cl (4.6 g, 85 mmol) were charged to a 250 mL round-bottomed flask. This mixture was warmed to 80° C. for 4 hours, and then allowed to cool to room temperature. The mixture was filtered through GF/F filter paper and concentrated to remove EtOH. The organic layers were extracted with EtOAc (2×100 mL), dried over Na2SO4, and concentrated to get 3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-amine (2.7 g, 74%) of crude product as an oil.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was filtered through GF/F
  3. filtrationfilter paper
  4. concentrationconcentrated
  5. customto remove EtOH
  6. extractionThe organic layers were extracted with EtOAc (2×100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b7c2aa80b7fb409eada9ea521cd95c19
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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