N,N'-Dimethylethylenediamine → HCID 86296099, compound

HRID 513246Notes

Reaction equation

HRID 513246 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:5]([CH3:24])[O:4][N:3]=1.I[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O1CCOCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[C:11](=[O:16])[C:10]3([CH3:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:5]([CH3:24])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 707143-Iodopyridine2×HCID 86296098HCID 86296098, compound

Product 1

HCID 86296099HCID 86296099, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

5-(3,5-Dimethyl-isoxazol-4-yl)-3-methyl-3-phenyl-1,3-dihydro-indol-2-one (100 mg, 0.314 mmol), 3-iodopyridine (71 mg, 0.346 mmol), copper (I) iodide (60 mg, 0.314 mmol), N,N′-dimethylethylenediamine (41.5 mg, 0.471 mmol), potassium carbonate (217 mg, 1.571 mmol) are added to a microwave vessel. Dioxane (5 mL) is added and the mixture heated to 140° C. for 30 minutes in a microwave reactor. A further 3-iodopyridine (35 mg, 0.173 mmol) and copper (I) iodide (12 mg, 0.063 mmol) are added. The mixture is again heated to 140° C. for 30 minutes in a microwave reactor. The reaction mixture is filtered. The filtrate is washed with dichloromethane. The volatiles are evaporated and the residue purified using reversed phase HPLC. This afforded the desired product.

Workup

  1. temperatureThe mixture is again heated to 140° C. for 30 minutes in a microwave reactor
  2. filtrationThe reaction mixture is filtered
  3. washThe filtrate is washed with dichloromethane
  4. customThe volatiles are evaporated
  5. customthe residue purified

Sources & evidence

ORD record
ord-87dc3f0e784540d5b01549e228a39437
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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