Cesium carbonate → HCID 24851818, compound

HRID 500553Notes

Reaction equation

HRID 500553 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]2[N:19]([CH3:20])[C:18](S(C)(=O)=O)=[N:17][N:16]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:27]=[C:28]([C:32]2[O:36][N:35]=[C:34]([CH:37]([OH:39])[CH3:38])[CH:33]=2)[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]2[N:19]([CH3:20])[C:18]([O:39][CH:37]([C:34]3[CH:33]=[C:32]([C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[CH:27]=4)[O:36][N:35]=3)[CH3:38])=[N:17][N:16]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 24851706HCID 24851706, compoundHCID 57528604HCID 57528604, compound

Product 1

HCID 24851818HCID 24851818, compoundYield 89%

Conditions

Temperature
65 °C

Procedure

The title compound from example 29.1 (103 mg, 0.298 mmol), the title compound from example 7.1 (100 mg, 0.4471 mmol) and cesium carbonate (291 mg, 0.894 mmol) were combined in a screw cap vial which was purged with nitrogen. Dimethylformamide (3 mL) was added and the reaction was stirred at 65° C. overnight. The reaction mixture was then cooled to room temperature, diluted with water and extracted three times with dichloromethane. The combined organics were dried over magnesium sulfate, filtered and concentrated, then chromatographed in dichloromethane followed by ethyl acetate on silica gel to give the title compound (129.4 mg, 58%).

Workup

  1. customcap
  2. customwhich was purged with nitrogen
  3. additionDimethylformamide (3 mL) was added
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. additiondiluted with water
  6. extractionextracted three times with dichloromethane
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed in dichloromethane

Sources & evidence

ORD record
ord-cad4fba8a79f4b82bf83eb6a97eca1c3
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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