Sodium Carbonate → 3-Methyl-2H-pyrazolo(3,4-b)pyridine-5-carboxylic acid

HRID 1880396Notes

Reaction equation

HRID 1880396 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.O1CCOCC1.[C:18](=O)([O-:20])[O-:19].[Na+].[Na+]>O.CCOC(C)=O>[CH3:11][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:18]([OH:20])=[O:19])[CH:3]=2)[NH:8][N:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 178434433HCID 178434433, compound

Product 1

HCID 1784344633-Methyl-2H-pyrazolo(3,4-b)pyridine-5-carboxylic acidYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
165 °C

Procedure

A microwave tube was charged with 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (515 mg, 2.43 mmol), dioxane (2 mL), Hermann's catalyst (72.1 mg, 0.12 mmol) and a solution of sodium carbonate (772 mg, 7.29 mmol) in water (5 mL). The mixture was stirred for 20 sec, heated at 165° C. for 15 minutes in a microwave reactor at very high absorption setting. The reaction was vented before handling. The mixture was diluted with EtOAc and stirred for 5 minutes before filtering through diatomaceous earth to provide the title compound (124 mg, 29%).

Workup

  1. stirringstirred for 5 minutes
  2. filtrationbefore filtering through diatomaceous earth

Sources & evidence

ORD record
ord-935e8adb986741c399a8837546262ba0
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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