Potassium Carbonate → HCID 46220334, compound

HRID 241962

Reaction equation

HRID 241962 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][NH:12]3)[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([OH:31])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:31][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][NH:12]3)[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 162513,4-DimethoxyphenolHCID 580832341H-Pyrazolo[3,4-b]pyridine, 4-chloro-6-(1H-indazol-4-yl)-1-methyl-

Product 1

HCID 46220334HCID 46220334, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
155 °C

Procedure

4-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (0.040 g, 0.141 mmoles) was dissolved in 2 mL DMF. 3,4-Dimethoxyphenol 8c (0.035 g, 0.281 mmol) was added followed by the addition of potassium carbonate (0.2 g, 1.41 mmol) and the resultant reaction mixture was heated in a microwave at 155° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and filtered. The organic portions were washed with saturated sodium bicarbonate solution followed by brine, dried over anhydrous sodium sulfate, solvent removed and purified to obtain 108 as a white solid (10 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 10.13 (s, 1H), 8.81 (s, 1H), 7.76-7.40 (m, 4H), 7.14-6.87 (m, 2H), 6.87-6.65 (m, 2H), 4.25 (d, J=16.2, 3H), 3.91 (d, J=31.0, 6H) MS (ESI) m/z 402.2 (M+1)+

Workup

  1. customthe resultant reaction mixture
  2. filtrationfiltered
  3. washThe organic portions were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate, solvent
  5. customremoved
  6. custompurified

Sources & evidence

ORD record
ord-3c9ca5a119284ba48f8e1e057f79463d
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Linked notes

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