Cesium carbonate → HCID 71622134, compound

HRID 2099022Notes

Reaction equation

HRID 2099022 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:27](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.ClCCl>[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]([CH3:27])[CH2:22][CH2:21]1)[CH:14]=2

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 71621990HCID 71621990, compound

Product 1

HCID 71622134HCID 71622134, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

100 mg (0.28 mmol) 3-Benzothiazol-2-yl-7-piperazin-1-yl-chromen-2-one were dissolved in 15 mL DMF and treated under argon with 183 mg (2 eq.) cesium carbonate, cooled below 5° C. and treated with 1 eq (0.018 mL) Mel. After stirring for 4 h, the reaction mixture is diluted with 100 mL dichloromethane and washed twice with ice-water. The organic phase is evaporated and the residue column chromatographed (silica gel, dichloromethane/EtOH 9:1). Recrystallization from methanol/dichloromethane yields 50 mg (47%) desired product as an orange powder.

Workup

  1. temperaturecooled below 5° C.
  2. additiontreated with 1 eq (0.018 mL) Mel
  3. washwashed twice with ice-water
  4. customThe organic phase is evaporated
  5. customthe residue column chromatographed (silica gel, dichloromethane/EtOH 9:1)
  6. customRecrystallization from methanol/dichloromethane

Sources & evidence

ORD record
ord-962f677f8f5d4da8804e192289d9fb6e
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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