Methanol → HCID 178520053, compound

HRID 1943925Notes

Reaction equation

HRID 1943925 reaction equation
[OH-].[Na+].[CH:3]1([C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[N:9]=2)=[O:7])[CH2:5][CH2:4]1.CO>C1COCC1.[Cl-].[NH4+]>[CH:3]1([C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)=[O:7])[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67088862HCID 67088862, compound

Product 1

HCID 178520053HCID 178520053, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

NaOH (0.39 mL, 0.39 mmol) was added to cyclopropyl(5-nitro-1-tosyl-1H-pyrazolo[3,4-b]pyridin-3-yl)methanone (0.076 g, 0.20 mmol) in THF:MeOH (1 ml, 4:1). After the compound dissolved in about 5 minutes, the reaction was complete. The reaction mixture was diluted with aqueous ammonium chloride (8 mL) and extracted with EtOAc (3×4 mL). The combined organic layers were dried over sodium sulfate, decanted, and concentrated to provide cyclopropyl(5-nitro-1H-pyrazolo[3,4-b]pyridin-3-yl)methanone (0.040 g, 0.17 mmol, 88% yield).

Workup

  1. dissolutionAfter the compound dissolved in about 5 minutes
  2. extractionextracted with EtOAc (3×4 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b218a4d5317a40989b3d9fb63d308ce3
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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