Hydrochloric Acid → HCID 178468965, compound

HRID 82022Notes

Reaction equation

HRID 82022 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:15]=[N:14][NH:13][C:8]=2[N:9]=[C:10]([Cl:12])[CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])O.[Na+].[I:21]I.S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:15]([I:21])=[N:14][NH:13][C:8]=2[N:9]=[C:10]([Cl:12])[CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807Iodine2×HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 86678157ETHYL6-CHLORO-1H-PYRAZOLO[3,4-B]PYRIDINE-4-CARBOXYLATE

Product 1

HCID 178468965HCID 178468965, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 1 L single necked flask were charged 6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (10 g, 44.3 mmol) and dioxane (400 ml). To this resulting suspension were added a saturated solution of sodium hydrogen carbonate (0.5M, 260 ml) and iodine (11.2 g, 44.3 mmol). The reaction mixture was stirred at room temperature for 24 hours, iodine was then added (25 g, 97.5 mmol) and stirring was pursued for 48 hours. Next an aqueous sodium thiosulfate solution (0.9M) was added until complete decolouration and was poured into a solution of ice and HCl at pH=2. The mixture was filtered to afford the title compound as a yellow solid (14.7 g, 95%).

Workup

  1. stirringstirring
  2. waitwas pursued for 48 hours
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-0feb0072c1d8407692aef2d36ab0e5e5
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Reaction notes

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