Potassium Carbonate → HCID 18447168, compound

HRID 1269858Notes

Reaction equation

HRID 1269858 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)[CH2:3][CH2:2]1.Br[CH2:18][CH2:19][O:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:21][O:20][CH2:19][CH2:18][N:1]1[CH2:2][CH2:3][CH:4]([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 516892Sodium BicarbonateHCID 229334675-(piperidin-4-yloxy)-1H-indazole

Product 1

HCID 18447168HCID 18447168, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 5-(4-piperidinyloxy)-1H-indazole (100 mg, 0.460 mmol) obtained in Example 42 in N,N-dimethylformamide (3 ml) were added (2-bromoethyl)methyl ether (76.8 mg, 0.552 mmol) and potassium carbonate (159 mg, 1.15 mmol), and the resulting mixture was stirred overnight at room temperature. Then, the reaction solution was cooled to 0° C. and a saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol) to obtain 5-{[1-(2-methoxyethyl)piperidin-4-yl]oxy}-1H-indazole (52 mg, 41%).

Workup

  1. temperatureThen, the reaction solution was cooled to 0° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-4007c02a6324427e800ea67bf4883015
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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