Potassium Carbonate → HCID 178508012, compound

HRID 1943867Notes

Reaction equation

HRID 1943867 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[N:10](S(C2C=CC(C)=CC=2)(=O)=O)[N:9]=1>CO.O>[Br:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[NH:10][N:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67089070HCID 67089070, compound

Product 1

HCID 178508012HCID 178508012, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

K2CO3 (0.233 g, 1.68 mmol) was added to a solution of 3-bromo-1-tosyl-1H-pyrazolo[3,4-b]pyridin-5-amine (0.206 g, 0.56 mmol) in MeOH/H2O (3:1, 8 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated. The resulting residue was taken up in water (10 mL), and the pH was adjusted to about 7 with acetic acid. The aqueous layer was extracted with ethyl acetate (3×50 mL) The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (1:4) to give 3-bromo-1H-pyrazolo[3,4-b]pyridin-5-amine (0.036 g, 30%) as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL) The combined organic layers
  3. customwere dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexanes/ethyl acetate (1:4)

Sources & evidence

ORD record
ord-1327b6ea4c7341b9a30cb2635b798837
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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