Potassium Carbonate → ethyl 1-isopropyl-6-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1501581Notes

Reaction equation

HRID 1501581 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(#N)C>[CH:11]([N:8]1[C:6]2[N:7]=[C:2]([N:29]3[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]3)[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]=2[CH:10]=[N:9]1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 86703408ethyl 6-bromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 68294946ethyl 1-isopropyl-6-(4-methylpiperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of ethyl 6-bromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (0.3 g, 0.964 mmol) in acetonitrile (10 mL), K2CO3 (0.26 g, 1.93 mmol) and 1-methylpiperazine (0.289 g, 2.892 mmol) was added. The reaction mixture was refluxed for 3 h. On completion of reaction, acetonitrile was removed under reduced pressure and water was added to it. Extraction was carried out using DCM; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to obtain the desired intermediate (0.32 g, 94.9%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  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

Sources & evidence

ORD record
ord-efedc8ce401c4badae9e0a61f84c7a53
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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