Cesium carbonate → HCID 23447918, compound

HRID 2185922Notes

Reaction equation

HRID 2185922 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC(S(O[CH2:39][C:40]([F:43])([F:42])[F:41])(=O)=O)=CC=1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([O:20][CH2:39][C:40]([F:43])([F:42])[F:41])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 23447878HCID 23447878, compound

Product 1

HCID 23447918HCID 23447918, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 2.83g of Compound 9A, 6.05 g of cesium carbonate and 2.95 g of 2,2,2-trifluoroethyl p-toluenesulphonate in 60 mL of acetonitrile was refluxed for 16 hours. The solvent was evaporated at reduced pressure; 90 mL of brine was added to the residue and the mixture was extracted with 3×40 mL of ethyl acetate. The organic layer was washed with 3×20 mL of water and 20 mL of brine, and dried over sodium sulphate. The solvent was removed at reduced pressure and the residue purified by flash chromatography (petroleum ether/ethyl acetate gradient 95:5 to 80:20). The solvents were removed in vacuo to give 1.86 g (52%) of Compound 9B as a white solid. M.p. (98) 102-105° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customThe solvent was evaporated at reduced pressure
  3. addition90 mL of brine was added to the residue
  4. extractionthe mixture was extracted with 3×40 mL of ethyl acetate
  5. washThe organic layer was washed with 3×20 mL of water and 20 mL of brine
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was removed at reduced pressure
  8. customthe residue purified by flash chromatography (petroleum ether/ethyl acetate gradient 95:5 to 80:20)
  9. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-51c66a7089374a5e85558fb7a7b53252
Source dataset
uspto-grants-2002_06
Patent number
US06403594B1

Reaction notes

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