Potassium Carbonate → HCID 18447087, compound

HRID 1269830Notes

Reaction equation

HRID 1269830 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)[CH2:2]1.I[CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:13]1[C:14]2[C:10](=[CH:9][C:8]([O:7][CH:3]3[CH2:4][CH2:5][CH2:6][N:1]([CH2:18][CH2:19][OH:20])[CH2:2]3)=[CH:16][CH:15]=2)[CH:11]=[N:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 229334705-[(Piperidin-3-yl)oxy]-1H-indazole

Product 1

HCID 18447087HCID 18447087, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the 5-(piperidin-3-yloxy)-1H-indazole (43 mg, 0.20 mmol) obtained in Example 377, 2-iodoethanol (84 mg, 0.49 mmol), potassium carbonate (70 mg, 0.50 mmol) and N,N-dimethylformamide (1 ml) was stirred at room temperature for 24 hours. The precipitate was removed by filtration and the solvent was distilled off as an azeotrope with toluene. The residue oil was purified by a silica gel column chromatography (eluent: ethyl acetate/triethylamine/ethanol=20/1/1) to obtain 2-[3-(1H-indazol-5-yloxy)piperidin-1-yl]ethanol (17 mg, 32%).

Workup

  1. customThe precipitate was removed by filtration
  2. distillationthe solvent was distilled off as an azeotrope with toluene
  3. customThe residue oil was purified by a silica gel column chromatography (eluent: ethyl acetate/triethylamine/ethanol=20/1/1)

Sources & evidence

ORD record
ord-81101633bea04796bf77b730117a6211
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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