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

HRID 589347Notes

Reaction equation

HRID 589347 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:10]=2)=[CH:18][CH:19]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 178526610HCID 178526610, compound

Product 1

HCID 89590255ethyl 2-[3-(4-nitrobenzyl)-1H-indazol-1-yl]acetateYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a dry reaction vessel, 2.15 g (8.49 mmol) 3-(4-nitrobenzyl)-1H-indazole, 10 mL DMF, 1.70 g (10.2 mmol) ethyl bromoacetate, 5.54 g (17.0 mmol) cesium carbonate were respectively added, and reacted at room temperature overnight. It was chromatographed on a column to obtain 1.4 g red solid, at a yield of 48.5%.

Workup

  1. additionwere respectively added
  2. customreacted at room temperature overnight
  3. customIt was chromatographed on a column

Sources & evidence

ORD record
ord-9520289e1d3d438b8be038dc166cd41b
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

Loading…