Cesium carbonate → HCID 136350684, compound

HRID 1409329Notes

Reaction equation

HRID 1409329 reaction equation
[NH:1]1[C:5]2[NH:6][C:7]([C:9]([O:11]CC)=[O:10])=[CH:8][C:4]=2[CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)C.O>[NH:1]1[C:5]2[NH:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:4]=2[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 10796Cesium carbonate2×HCID 136377295HCID 136377295, compound

Product 1

HCID 136350684HCID 136350684, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

Ethyl 1,6-dihydropyrrolo[2,3-c]pyrazole-5-carboxylate (1.328 mmol, 0.238 g) was dissolved in ethanol (10 ml). Cesium carbonate (2.66 mmol, 0.866 g) dissolved in water (2 ml) was added and the resulting mixture was stirred at RT for a day after which more cesium carbonate (2.66 mmol, 0.866 g) dissolved in water (2 ml) was added. The temperature was raised to 80° C. for 7 h. Ethanol was evaporated and the residue was diluted with water. pH was adjusted to 4 with 2 M HCl and extracted three times with EtOAc and washed with water. The combined organics were dried, filtered and evaporated. 0.041 g of the title compound was obtained. LC-MS [M+1]: 152.

Workup

  1. additionwas added
  2. additionwas added
  3. customEthanol was evaporated
  4. additionthe residue was diluted with water
  5. extractionextracted three times with EtOAc
  6. washwashed with water
  7. customThe combined organics were dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-ceed4b0c24cf4a40b54ffe7e2c81bc1d
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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