Cesium carbonate → HCID 23003167, compound

HRID 396202Notes

Reaction equation

HRID 396202 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:19]=1[CH2:20]Br>CN(C)C=O>[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:19]=1[CH2:20][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 160545-HydroxyindoleHCID 301591-Bromomethyl-2,6-dichlorobenzene

Product 1

HCID 23003167HCID 23003167, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-hydroxyindole (5.0 g, 37.6 mmol) in dimethylformamide (200 mL) at room temperature was added cesium carbonate (18.4 g, 56.3 mmol). The reaction mixture was stirred at 60° C. for 30 min followed by the addition of 2,6-dichlorobenzyl bromide (9.0 g, 37.6 mmol). After stirring at 60° C. for 16 h, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried (Na2SO4). Purification by flash column chromatography (silica gel, hexane/ethyl acetate) yielded a clear oil (8.05 g, 73%). MS(ES) m/e 292.0 [M+H]+.

Workup

  1. stirringAfter stirring at 60° C. for 16 h
  2. customthe reaction solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customPurification by flash column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-75ffa556e8344d3f998a5e71be118a84
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

Loading…