Sodium Trifluoroacetate → HCID 11745639, compound

HRID 1449621Notes

Reaction equation

HRID 1449621 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1I.[F:12][C:13]([F:18])([F:17])C([O-])=O.[Na+]>CN1CCCC1=O.O.[Cu]I>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:13]([F:18])([F:17])[F:12]

Participants

6

Reactant 2

HCID 517019Sodium TrifluoroacetateHCID 110650591H-Indole, 2-iodo-1-methyl-

Product 1

HCID 11745639HCID 11745639, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-methyl-2-iodoindole (4.40 g, 17.3 mmole), sodium trifluoroacetate (24.0 g, 176.5 mmole) and copper(I) iodide (17.1 g, 89.8 mmole) in N-methylpyrrolidone is heated at 160° C. for 6 hours, cooled to room temperature, diluted with water and filtered through diatomaceous earth to remove copper salts. The filtrate is extracted with ether. The extracts are combined, washed with water, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is chromatographed using silica gel and 4:1 hexanes:ethyl acetate as eluent to give the title product as a pale yellow oil which crystallized on standing, 119 g (37% yield), mp 28°-32° C., identified by IR, 1HNMR and 19FNMR analyses.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. customto remove copper salts
  4. extractionThe filtrate is extracted with ether
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give a residue
  9. customThe residue is chromatographed

Sources & evidence

ORD record
ord-2663fa617e9048648adb15c309d5b1e1
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

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