Dimethylformamide → HCID 57566815, compound

HRID 1819344Notes

Reaction equation

HRID 1819344 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][NH:20][C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:24]1[CH:25]=[C:26]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:28][CH:29]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C=O)C>[Cu]I.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]2[CH2:21][N:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=3)[C:19](=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 125741-Iodo-3-nitrobenzeneHCID 62657Potassium Phosphate, TribasicHCID 145371514-[3-(Benzyloxy)-4-methoxyphenyl]pyrrolidin-2-one

Product 1

HCID 57566815HCID 57566815, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a round bottom flask was added 4-(3-benzyloxy-4-methoxyphenyl)-pyrrolidin-2-one (1.76 g, 5.9 mmol), 3-iodonitrobenzene (2.64 g, 10.6 mmol), K3PO4 (2.79 g, 13 mmol), trans-cyclohexanediamine (50 μL), DMF (8 mL) and dioxane (8 mL). The mixture was stirred under N2 for 5 min before the addition of CuI (150 mg). After heating to 110° C. for 20 h, the mixture was cooled to r.t. After filtration, the reaction mixture was diluted with EtOAc (100 mL), washed with saturated NH4Cl, brine and dried over Na2SO4. Concentration and purification by column chromatography on silica gel (EtOAc:hexane=1:3) gave 1.4 g of the desired product. Yield: 57%.

Workup

  1. temperaturethe mixture was cooled to r.t
  2. filtrationAfter filtration
  3. additionthe reaction mixture was diluted with EtOAc (100 mL)
  4. washwashed with saturated NH4Cl, brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration and purification by column chromatography on silica gel (EtOAc:hexane=1:3)

Sources & evidence

ORD record
ord-264eda41177140659e93766d32a0870e
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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