2-Bromopropane → HCID 86703431, compound

HRID 1854080Notes

Reaction equation

HRID 1854080 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]2[C:10]([CH2:11][CH3:12])=[N:9][NH:8][C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:25]([CH3:27])[CH3:26]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]2[C:10]([CH2:11][CH3:12])=[N:9][N:8]([CH:25]([CH3:27])[CH3:26])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178468568HCID 178468568, compound

Product 1

HCID 86703431HCID 86703431, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl 6-bromo-3-ethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (0.45 g, 1.51 mmol) was suspended in acetonitrile (5 mL) and K2CO3 (0.312 g, 2.26 mmol) and 2-bromopropane (0.372 g, 3.02 mmol) was added to it. The reaction mixture was refluxed for overnight. On completion of reaction, acetonitrile was removed under reduced pressure and water was added to it. Extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to give the desired intermediate (0.4 g, 87.7%).

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. customwas removed under reduced pressure and water
  3. additionwas added to it
  4. extractionExtraction
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customSolvent was removed under reduced pressure and residue
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cfecd1c637f24d7eb379a0f0d5406f42
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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