Water → Ethyl (6-chloro-1-methyl-1H-indazol-3-yl)acetate

HRID 82216Notes

Reaction equation

HRID 82216 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9][NH:10]2)=[CH:6][CH:5]=1.I[CH3:20].O>C1COCC1>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9][N:10]2[CH3:20])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178470796HCID 178470796, compound

Product 1

HCID 70847731Ethyl (6-chloro-1-methyl-1H-indazol-3-yl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (24 mg, 0.602 mmol, 60% in oil) was added to ethyl (6-chloro-1H-indazol-3-yl)acetate (Preparation 168, 120 mg, 0.502 mmol) in THF (4 mL) at 0° C. and the mixture was stirred for 30 minutes. Then iodomethane (0.09 mL, 1.508 mmol) was added. The mixture was stirred at room temperature for 30 mins then water (4 mL) was added. The mixture was evaporated in vacuo and the aqueous residue was acidified with aqueous HCl (6 M). This was extracted with ethyl acetate (10 mL) and the organic phase was dried over sodium sulphate and evaporated in vacuo to afford the title compound as a white solid in 100% yield, 150 mg.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 mins
  2. customThe mixture was evaporated in vacuo
  3. extractionThis was extracted with ethyl acetate (10 mL)
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-577d074b4c464056aa9e8b64afcdfa8d
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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