Cesium carbonate → methyl 2-[1-(4-nitrobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate

HRID 589409Notes

Reaction equation

HRID 589409 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1)([O-:23])=[O:22]>O1CCCC1>[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:2]2)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 178499647HCID 178499647, compound

Product 1

HCID 89590260methyl 2-[1-(4-nitrobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetateYield 17.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(1H-pyrazolo[3,4-b]pyridin-3-yl)acetate (250 mg, 1.31 mmol), cesium carbonate (850 mg, 2.61 mmol), were added into 30 mL tetrahydrofuran, and stirred at room temperature for 15 minutes. Then 4-nitrobenzyl bromide (283 mg, 1.31 mmol) was added, and reacted at room temperature for 12 hours. It was filtered to remove the solid. The filtrate was rotate evaporated to dryness, and chromatographed on a column (PE:EA=10:1) to obtain a light yellow solid 75 mg, at a yield of 17.6%.

Workup

  1. customreacted at room temperature for 12 hours
  2. filtrationIt was filtered
  3. customto remove the solid
  4. customThe filtrate was rotate evaporated to dryness
  5. customchromatographed on a column (PE:EA=10:1)

Sources & evidence

ORD record
ord-4ebcdc6d5e4640bb9ec35ef9e6cb2a6c
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

Loading…