N,N'-Dimethylethylenediamine → HCID 67036298, compound

HRID 1623429Notes

Reaction equation

HRID 1623429 reaction equation
[C:1]1([C:7](=[C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].CNCCNC.I[C:32]1[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=1)[C:35]([O:37][CH2:38][CH3:39])=[O:36]>[Cu]I.C(#N)C>[CH2:38]([O:37][C:35](=[O:36])[C:34]1[CH:40]=[CH:41][CH:42]=[C:32]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9](=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:8])[C:10]2=[O:18])[CH:33]=1)[CH3:39]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 143542Ethyl 3-iodobenzoateHCID 23962083HCID 23962083, compound

Product 1

HCID 67036298HCID 67036298, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 3-(1-phenyl-ethylidene)-1,3-dihydro-indol-2-one (352.7 mg, 1.5 mmol), and K2CO3 (276 mg, 2.0 mmol), evacuated, and backfilled with argon. N,N′-dimethylethylenediamine (11 uL, 0.10 mmol, 10 mol %), ethyl 3-iodobenzoate (278.8 mg, 1.01 mmol), and acetonitrile (1.5 ml) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80° C. for 23 h. The reaction was monitored by HPLC. When the reaction was finished, the solvent was removed under reduced pressure. The residue was separated by flash chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether) to give 3-[2-oxo-3-(1-phenyl-ethylidene)-2,3-dihydro-indol-1-yl]-benzoic acid ethyl ester as yellow powder (344 mg, 90%). 1H NMR (400 MHz, CDCl3) δppm 1.42 (t, J=7.20 Hz, 3H) 2.87 (s, 3H) 4.42 (q, J=7.07 Hz, 2H) 6.25 (d, J=7.58 Hz, 1H) 6.68-6.78 (m, 2H) 7.09 (t, J=7.71 Hz, 1H) 7.34-7.40 (m, 2H) 7.47-7.58 (m, 3H) 7.62-7.72 (m, 2H) 8.11-8.19 (m, 2H). MS calcd. for C25H21NO3 383, obsd. (ESI+) [(M+H)+] 383.9.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was separated by flash chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-281b4bb7335b4ebbb0f70986bc2b517a
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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