Ethyl chloroacetate → ethyl 2-(3-bromo-4-nitro-1H-indazol-1-yl)acetate

HRID 79454Notes

Reaction equation

HRID 79454 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:3]=1

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 178526560HCID 178526560, compound

Product 1

HCID 67261176ethyl 2-(3-bromo-4-nitro-1H-indazol-1-yl)acetateYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-4-nitro-1H-indazole (Preparation B; 1.00 g, 4.13 mmol) in anhydrous DMF (20 mL) was treated at ambient temperature with potassium carbonate (2.28 g, 16.5 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes and ethyl 2-chloroacetate (0.53 g, 4.34 mmol) was added dropwise. Stirring was continued under nitrogen for 16 hours. The reaction mixture was diluted with excess water and extracted multiple times with DCM and EtOAc. The combined extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the product (1.21 g) as a brown solid.

Workup

  1. stirringStirring
  2. waitwas continued under nitrogen for 16 hours
  3. extractionextracted multiple times with DCM and EtOAc
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1affbb0fe1b444fab4adfa74291fec79
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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