Cesium carbonate → HCID 86599839, compound

HRID 2099018Notes

Reaction equation

HRID 2099018 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](=[O:26])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH:14]=2.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:34][CH2:35][OH:36]>CN(C=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](=[O:26])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([N:20]1[CH2:25][CH2:24][N:23]([CH2:34][CH2:35][OH:36])[CH2:22][CH2:21]1)[CH:14]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12225IodoethanolHCID 71621990HCID 71621990, compound

Product 1

HCID 86599839HCID 86599839, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

240 mg crude 3-benzothiazol-2-yl-7-piperazin-1-yl-chromen-2-one in 10 mL DMF are stirred for 72 h at room temperature in the presence of 858 mg (at least 4 eq.) cesium carbonate and 0.103 mL (at least 2 eq.) 2-iodoethanol. The reaction mixture is extracted with ethyl acetate and a saturated solution of sodium carbonate and washed with brine. The combined organic phases are dried with sodium sulphate and evaporated. The residue is column chromatographed (silica gel, dichloromethane/methanol 95:5+1% conc. NH4OH) to yield 70 mg (26%) desired product as an orange solid.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. washa saturated solution of sodium carbonate and washed with brine
  3. dry with materialThe combined organic phases are dried with sodium sulphate
  4. customevaporated
  5. customchromatographed (silica gel, dichloromethane/methanol 95:5+1% conc. NH4OH)

Sources & evidence

ORD record
ord-9b60706dc5304f028f75a7ab89725982
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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