Potassium Carbonate → HCID 86652504, compound

HRID 1943938Notes

Reaction equation

HRID 1943938 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[N:7](S(C2C=CC(C)=CC=2)(=O)=O)[N:6]=1.C([O-])([O-])=O.[K+].[K+]>CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[F:1][CH2:2][CH2:3][O:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[NH:7][N:6]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86652505HCID 86652505, compound

Product 1

HCID 86652504HCID 86652504, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-(2-fluoroethoxy)-5-nitro-1-tosyl-1H-pyrazolo[3,4-b]pyridine (0.273 g, 0.718 mmol) and aqueous K2CO3 (1.8 mL, 2M) in MeOH (14 mL) was heated at 55° C. for 1 hour. After cooling to room temperature, the mixture was diluted with 10% aqueous citric acid, extracted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, and concentrated to give 3-(2-fluoroethoxy)-5-nitro-1H-pyrazolo[3,4-b]pyridine. The material was purified by silica gel flash column chromatography (1% MeOH in CH2Cl2) to afford 3-(2-fluoroethoxy)-5-nitro-1H-pyrazolo[3,4-b]pyridine along with a byproduct. LRMS (ESI pos) m/e 207.0 (M−F).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9eef0c425a6d49b3a44022be3cbe2867
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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