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

HRID 589383Notes

Reaction equation

HRID 589383 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.C(=O)([O-])[O-].[Cs+].[Cs+].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23]>O1CCCC1>[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29][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:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 178470794HCID 178470794, compound

Product 1

HCID 89590252ethyl 2-[1-(4-nitrobenzyl)-1H-indazol-3-yl]acetateYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(1H-indazol-3-yl)acetate (9.78 g, 47.9 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL). Cesium carbonate (46.81 g, 143.7 mmol) was added, and stirred at room temperature for half an hour. Then p-nitro benzyl bromide (10.36 g, 47.96 mmol) was added, reacted for 16 hours, and then the solid was filtered. The filtrate was concentrated, chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a yellow solid 12.68 g, at a yield of 78.1%.

Workup

  1. customreacted for 16 hours
  2. filtrationthe solid was filtered
  3. concentrationThe filtrate was concentrated
  4. customchromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-31ec5e7cee1143e090811fcf2ac1f993
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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