2-Bromopropane → HCID 86703418, compound

HRID 1909224Notes

Reaction equation

HRID 1909224 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2[C:10]([CH3:11])=[N:9][NH:8][C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:24]([CH3:26])[CH3:25]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:24]([CH3:26])[CH3:25])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178468567HCID 178468567, compound

Product 1

HCID 86703418HCID 86703418, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl 6-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (1 g, 3.52 mmol) was suspended in acetonitrile (10 mL) and K2CO3 (0.728 g, 5.28 mmol) and 2-bromopropane (0.866 g, 7.04 mmol) was added to it. The reaction mixture was refluxed for overnight. On completion of reaction, acetonitrile was removed under reduced pressure and water added to it. Extraction was carried out using ethyl acetate and 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 obtain the desired intermediate (0.61 g, 53.5%). Structure was confirmed by NOE.

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. customwas removed under reduced pressure and water
  3. additionadded 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-aa868d0d98864ca090bd520feaae2dda
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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