Sodium hydride → ethyl 2-[1-(4-nitrobenzyl)-1H-indazol-3-yl]acetate

HRID 589364Notes

Reaction equation

HRID 589364 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1.[H-].[Na+].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19]>CN(C)C=O>[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 178470794HCID 178470794, compound

Product 1

HCID 89590252ethyl 2-[1-(4-nitrobenzyl)-1H-indazol-3-yl]acetateYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(1H-indazol-3-yl)acetate (408 mg, 2.0 mmol) was dissolved in N,N-dimethylformamide (20 mL), 60% sodium hydride (96 mg, 2.4 mmol) was added, and stirred at room temperature for half an hour. Then p-nitro benzyl bromide (475 mg, 2.2 mmol) was added, and reacted for 1 hour. Then, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, concentrated, chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a yellow solid 354 mg, at a yield of 52.1%.

Workup

  1. customreacted for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4bea93ba6fa54af28ce2094186267d73
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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