Cesium carbonate → HCID 59772701, compound

HRID 646257Notes

Reaction equation

HRID 646257 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:7](=[O:10])[CH2:8][CH3:9])[NH:5][CH:6]=1.I[CH2:12][C:13]([F:16])([F:15])[F:14].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([C:7](=[O:10])[CH2:8][CH3:9])[N:5]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 59772683HCID 59772683, compound

Product 1

HCID 59772701HCID 59772701, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(4-Iodo-1H-pyrrole-2-yl)-propan-1-one (3.8 g, 15.3 mmol), 2-Iodo-1,1,1-trifluoroethane (3.83 g, 18.3 mmol) and Cs2CO3 (5.96 g, 183 mmol) in 20 ml DMF is heated with stirring to 60° C. for until the reaction is finished (TLC). The mixture then is cooled to room temperature and partitioned between water (200 ml) and ether (100 ml), the ether phase is separated and dried with MgSO4. The product is purified by flash chromatography with solvent EtOAc/hexane (10/90) to afford the product as an oil which solidified upon standing 1.8 g (35%). 1HNMR (DMSO-d6): δ (ppm) 1.00 (t, 3H), 2.79 (q, 2H), 5.29 (q, 2H), 7.36 (s, 1H), 7.39 (s, 1H).

Workup

  1. temperatureis heated
  2. temperatureThe mixture then is cooled to room temperature
  3. custompartitioned between water (200 ml) and ether (100 ml)
  4. customthe ether phase is separated
  5. dry with materialdried with MgSO4
  6. customThe product is purified by flash chromatography with solvent EtOAc/hexane (10/90)

Sources & evidence

ORD record
ord-8c37354451f34a4db886da19ab25bb48
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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