Water → HCID 57621394, compound

HRID 541067Notes

Reaction equation

HRID 541067 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH2:21][O:22][CH3:23].O>CN(C=O)C>[CH3:23][O:22][CH2:21][CH2:20][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 225235-NitroindoleHCID 809722-Bromoethyl methyl ether

Product 1

HCID 57621394HCID 57621394, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitroindole (3.5 g; 21.6 mmol) in DMF (100 ml) was added Cs2CO3 (13.9 g; 42.6 mmol). The mixture thus obtained was stirred 1 h hour at room temperature then 1-bromo-2-methoxyethane (5.9 g; 42.6 mmol) was added dropwise. The resulting mixture was heated to 120° C. under stirring for 4 hours. After cooling, the mixture was poured into water (500 ml) and the crude product was filtered, dried under vacuum to give 1-(2-methoxyethyl)-5-nitro-1H-indole which was used in the following reaction without any further purification.

Workup

  1. customThe mixture thus obtained
  2. temperatureThe resulting mixture was heated to 120° C.
  3. stirringunder stirring for 4 hours
  4. temperatureAfter cooling
  5. filtrationthe crude product was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-89118111c49148e2beec46541801f2bc
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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