Water → HCID 67088863, compound

HRID 1943944Notes

Reaction equation

HRID 1943944 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.O>CN(C=O)C>[I:1][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]([CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178526797HCID 178526797, compound

Product 1

HCID 67088863HCID 67088863, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodo-5-nitro-1H-pyrazolo[3,4-b]pyridine (1.00 g, 3.45 mmol) and cesium carbonate (1.69 g, 5.17 mmol) were combined in dry DMF (35 mL). p-Methoxybenzyl chloride (0.702 mL, 5.17 mmol) was added to this mixture, and the mixture was stirred at room temperature for 22 hours. Water (200 mL) was then added to the reaction mixture, resulting in a precipitate, which was collected by filtration. The solids were triturated with 3:1 EtOAc/Et2O (50 mL) to give 3-iodo-1-(4-methoxybenzyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (1 g, 71%) as a solid.

Workup

  1. customresulting in a precipitate, which
  2. filtrationwas collected by filtration
  3. customThe solids were triturated with 3:1 EtOAc/Et2O (50 mL)

Sources & evidence

ORD record
ord-0b16c4ee38a94ea4bb50fdb6c01c093a
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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