Ethyl Acetate → tert-Butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)benzofuran-3-carboxylate

HRID 61883

Reaction equation

HRID 61883 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][C:8](=[O:21])[C:9]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[C:14]([I:20])[CH:13]=1)([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][C:31]=1[N+]([O-])=O.C(OCC)(=O)C>CN1C(=O)CCC1>[C:1]([O:5][C:6]([C:7]1[C:30]2[CH:31]=[CH:32][C:33]([C:34]#[N:35])=[CH:36][C:37]=2[O:21][C:8]=1[C:9]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[C:14]([I:20])[CH:13]=1)([CH3:11])[CH3:10])=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 66834434tert-butyl 4-(4-ethyl-3-iodophenyl)-4-methyl-3-oxopentanoate

Product 1

HCID 66835004tert-Butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)benzofuran-3-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

4-(4-Ethyl-3-iodo-phenyl)-4-methyl-3-oxo-pentanoic acid tert-butyl ester (1.00 g, 2.40 mmol) was dissolved in NMP (4 ml), added with cesium carbonate (1.56 g, 4.80 mmol, 2.0 eq.), and the mixture was stirred for 5 min. The NMP solution (2 ml) of 4-chloro-3-nitro-benzonitrile (542 mg, 2.88 mmol, 1.2 eq.) was added thereto, and the mixture was stirred at 50° C. for 64 hrs under nitrogen atmosphere. After cooling to room temperature, ethyl acetate (20 ml) was added and the organic layer was washed with saturated aqueous solution of ammonium chloride (20 ml). The organic layer was further washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (white amorphous, 320 mg, 26%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 64 hrs under nitrogen atmosphere
  2. washthe organic layer was washed with saturated aqueous solution of ammonium chloride (20 ml)
  3. washThe organic layer was further washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe drying agent was removed by filtration
  6. customthe residues obtained
  7. concentrationafter concentration under reduced pressure
  8. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4e5a2c03260648c7a8a120668540e2ae
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Linked notes

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