Water → HCID 89740321, compound

HRID 2206469Notes

Reaction equation

HRID 2206469 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22].O>CC(C)=O>[C:23]1([CH:21]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]2)[CH3:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 657476methyl 1H-indazole-3-carboxylate

Product 1

HCID 89740321HCID 89740321, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 1H-indazole-3-carboxylate (2.0 g, 11.4 mmol) in acetone (50 mL), were added potassium carbonate (1.6 g, 11.4 mmol) and (1-bromoethyl)benzene (2.2 g, 11.9 mmol). Then the mixture was refluxed for 12 hours. The reaction mixture was concentrated to give a residue. To the residue was added water (50 mL), extracted with dichloromethane (50 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to afford two isomers.

Workup

  1. temperatureThen the mixture was refluxed for 12 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto give a residue
  4. extractionextracted with dichloromethane (50 mL×3)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)
  10. customto afford two isomers

Sources & evidence

ORD record
ord-46018b8c8f23447292de64a3f9dcc08d
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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