Cesium carbonate → HCID 66920398, compound

HRID 1510076Notes

Reaction equation

HRID 1510076 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:46][O:47][CH2:48][CH2:49]Br>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:49][CH2:48][O:47][CH3:46])=[CH:22][CH:23]=3)[N:18]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:17]=2[O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 44158437HCID 44158437, compound

Product 1

HCID 66920398HCID 66920398, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The compound of example 8 (63.0 mg, 119 μmol) was dissolved in DMF, and cesium carbonate (116 mg, 358 μmol) and 2-bromoethyl methyl ether (13.5 μl, 143 μmol) were added. The reaction mixture was stirred at 50° C. for 3 h. The cooled mixture was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica gel chromatography (EA/HEP). 60.0 mg of the title compound were obtained.

Workup

  1. extractionextracted with EA
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (EA/HEP)

Sources & evidence

ORD record
ord-887cfc7426f441c0a0f21aee6cdd98a0
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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