Sodium Hydroxide → HCID 178419486, compound

HRID 389588Notes

Reaction equation

HRID 389588 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1.O(Br)[Br:11].[Na].BrBr.[OH-].[Na+].[Cl-].[NH4+]>O>[Br:11][C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:1][N:2]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24408BromineHCID 25517Ammonium ChlorideHCID 64514411H-Pyrazolo[3,4-c]pyridineHCID 86662424HCID 86662424, compound

Product 1

HCID 178419486HCID 178419486, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 1H-pyrazolo[3,4-c]pyridine (0.50 g, 3.5 mmol) in water (10 mL) was added a solution of sodium oxybromide (prepared by dropwise addition of bromine (0.25 mL) to sodium hydroxide solution (0.40 mg in 5 mL) at 0° C. over 5 min). The reaction mixture stirred for 1 h at 10° C. The mixture was then acidified to pH ˜5.5 with ammonium chloride, and extracted with ethyl acetate (3×20 mL). The combined organic fractions were dried over sodium sulfate and concentrated to afford 0.43 g (62%) of the title compound. 1H NMR (300 MHz, CD3OD): δ 7.79 (dd, J=1.5, 4.2 Hz, 1H), 8.32-8.33 (d, J=5.7 Hz, 1H), 9.07 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8eaa4b44964b4cc5b106a9d59b9c7fc4
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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