Potassium Carbonate → HCID 68513219, compound

HRID 589407Notes

Reaction equation

HRID 589407 reaction equation
Br[CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:4]=1.C(=O)([O-])[O-].[K+].[K+].[Si]([C:29]#[N:30])(C)(C)C.[OH-].[Na+]>C(#N)C>[C:29]([CH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:4]=1)#[N:30]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 68513219HCID 68513219, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridin-1-carboxylate (700 mg, 2.24 mmol), potassium carbonate (370 mg, 2.68 mmol) and TMSCN (265 mg, 2.67 mmol) were added into 10 mL acetonitrile, and heated to 60° C. and reacted for 9 hours. After completion of the reaction, it was cooled. 1 M sodium hydroxide solution 100 mL was added, and extracted with ethyl acetate 150 mL. The organic phase was washed with water, washed with saturated saline, dried over anhydrous sodium sulfate, rotate evaporated to dryness, and chromatographed on a column (PE:EA=20:1) to obtain a white solid 460 mg, at a yield of 79.5%

Workup

  1. customreacted for 9 hours
  2. customAfter completion of the reaction, it
  3. temperaturewas cooled
  4. extractionextracted with ethyl acetate 150 mL
  5. washThe organic phase was washed with water
  6. washwashed with saturated saline
  7. dry with materialdried over anhydrous sodium sulfate, rotate
  8. customevaporated to dryness
  9. customchromatographed on a column (PE:EA=20:1)

Sources & evidence

ORD record
ord-cb4eae59ee284467bc89215d5918a1fa
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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