Water → HCID 67088863, compound

HRID 1943927Notes

Reaction equation

HRID 1943927 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[I:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[NH:10][N:9]=1.Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.O>CN(C=O)C>[I:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[N:10]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:9]=1

Participants

6

Reactant 4

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

Product 1

HCID 67088863HCID 67088863, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (25.3 g, 77.6 mmol) was added to 3-iodo-5-nitro-1H-pyrazolo[3,4-b]pyridine (15 g, 52 mmol) in DMF (500 mL). Then 1-(chloromethyl)-4-methoxybenzene (10.57 mL, 77.58 mmol) was added, which was stirred at room temperature for 16 hours. Water (1 L) was then added to the reaction mixture, which resulted in a precipitate. The solids were collected by filtration and transferred into a flask with the aid of i-PrOH. The concentrate was triturated with EtOAc/Et2O (3:1 EtOAc/Et2O, 750 mL) to give 3-iodo-1-(4-methoxybenzyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (12.1 g, 29.5 mmol, 56.9%) as a solid.

Workup

  1. customresulted in a precipitate
  2. filtrationThe solids were collected by filtration
  3. customtransferred into a flask with the aid of i-PrOH
  4. customThe concentrate was triturated with EtOAc/Et2O (3:1 EtOAc/Et2O, 750 mL)

Sources & evidence

ORD record
ord-8a29673a304d433f807deb9136fad93c
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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