Water → Ethyl 6-benzyloxy-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

HRID 1873955Notes

Reaction equation

HRID 1873955 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[N:8]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:12][CH:13]=2)[N:8]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 136205191Ethyl 6-hydroxy-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

Product 1

HCID 59370773Ethyl 6-benzyloxy-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl6-hydroxy-1-(tetrahydro-2H-pyran-2-yl)-indazole-3-carboxylate (148 mg) which can be prepared according to the method described in Reference example 20, etc. was dissolved in dehydrated DMF (5.2 mL; manufactured by Kanto Chemical Co., Inc.), added with potassium carbonate (227 mg; manufactured by Sigma-Aldrich Co.) and benzyl bromide (73.6 μL; manufactured by Wako Pure Chemical Industries, Ltd.), followed by stirring for overnight at 60° C. After cooling to room temperature, the reaction solution was added to water, and then extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with ethyl acetate, and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography “COLUMN-A”; n-hexane:ethyl acetate=95:5→74:26) to obtain the title compound (187 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextraction
  3. washThe organic layer was washed twice with water and once with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography “COLUMN-A”

Sources & evidence

ORD record
ord-f5b782bed56a4647bd10ac3dbcfa18ce
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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