Potassium Carbonate → HCID 178492924, compound

HRID 1774711Notes

Reaction equation

HRID 1774711 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[N:9]=2)=[C:4]([O:32][CH3:33])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)[NH:10][N:9]=2)=[C:4]([O:32][CH3:33])[CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 90221180HCID 90221180, compound

Product 1

HCID 178492924HCID 178492924, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-(4-fluoro-2-methoxyphenyl)-4-(thiophen-3-yl)-1-tosyl-1H-pyrazolo[3,4-b]pyridine 27 (50 mg 0.102 mmol) in methanol (10 mL) and water (5 mL) was added potassium carbonate (0.204 mmol) and the RM was heated to 60° C. overnight. After completion of the SM the solvents was completely distilled off, diluted with water and extracted with chloroform twice. The organic layer was dried over sodium sulphate. The crude product was passed through 100-200 mesh silica gel eluting the pre compound at 28-30% ethyl acetate in hexane as eluent to get the pale yellow colored solid of compound 3-(4-fluoro-2-methoxyphenyl)-4-(thiophen-3-yl)-1H-pyrazolo[3,4-b]pyridine 28. 1H NMR (CDCl3) δ: 8.56(d,1H), 7.44(m,1H), 7.23(m,1H), 7.16(m,1H), 7.02(m,1H), 6.95(m,1H), 6.73(m,1H), 6.34(m,1H) and MS m/z=325.8.

Workup

  1. distillationAfter completion of the SM the solvents was completely distilled off
  2. additiondiluted with water
  3. extractionextracted with chloroform twice
  4. dry with materialThe organic layer was dried over sodium sulphate

Sources & evidence

ORD record
ord-86de92eb27a047ea9f827ef635fe7e59
Source dataset
uspto-grants-2016_02
Patent number
US09260426B2

Reaction notes

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