Cesium carbonate → HCID 67147503, compound

HRID 2426988Notes

Reaction equation

HRID 2426988 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([O:12][CH3:13])=[O:11])[CH:3]=[CH:2]1.I[C:15]1[CH:16]=[C:17]([Cl:21])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1CCCC1.CCOC(C)=O.Cl[Cu]>[Cl:21][C:17]1[CH:16]=[C:15]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][C:8]=3[C:10]([O:12][CH3:13])=[O:11])[CH:3]=[CH:2]2)[CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 122691-Chloro-3-iodobenzeneHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 676694Methyl indole-7-carboxylate

Product 1

HCID 67147503HCID 67147503, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 84541-MethylpyrrolidineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 1H-indole-7-carboxylate (0.175 g), 3-iodo-chlorobenzene (0.358 g), Cs2CO3 (0.490 g), CuCl (0.099 g), and 2,2,6,6-tetramethyl-3,5-heptanedione (0.04 mL) in 5 mL of N-methylpyrrolidine was heated at 120° C. for 3 days. The mixture was then diluted with 50 mL of EtOAc and filtered through a pad of silica gel. The filtrate was washed with 3×15 mL of water and dried over Na2SO4. After filtration and concentration, the residue was purified by Combiflash eluted with a gradient of EtOAc/hexane to give 0.1 g of the title compound.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. washThe filtrate was washed with 3×15 mL of water
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by Combiflash
  6. washeluted with a gradient of EtOAc/hexane

Sources & evidence

ORD record
ord-80c96a23ca6248bea823889af2ececd6
Source dataset
uspto-grants-2011_06
Patent number
US07968578B2

Reaction notes

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