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

HRID 589410Notes

Reaction equation

HRID 589410 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[C:11]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[N:10]2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[C:11]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[N:10]2)=[CH:23][CH:24]=1

Participants

4

Reactant 1

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

Product 1

HCID 89590257methyl 2-[1-(4-aminobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetateYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-[1-(4-nitrobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate (75 mg, 0.23 mmol) was dissolved in 10 mL tetrahydrofuran. 10% Pd/C (5 mg) was added, and reacted under hydrogen atmosphere for 2 hours. It was filtered, and the filtrate was rotate evaporated to dryness directly to obtain a white solid 58 mg, at a yield of 87%.

Workup

  1. customreacted under hydrogen atmosphere for 2 hours
  2. filtrationIt was filtered
  3. customthe filtrate was rotate evaporated to dryness directly

Sources & evidence

ORD record
ord-a5cf23920d464190b40ec5cd33dd522b
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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