N,N'-Dimethylethylenediamine → 1-(3-tert-butyl-5-iodo-4-methoxyphenyl)pyridin-2(1H)-one

HRID 530666Notes

Reaction equation

HRID 530666 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[OH:7].[C:8]([C:12]1[CH:17]=[C:16](I)[CH:15]=[C:14]([I:19])[C:13]=1[O:20][CH3:21])([CH3:11])([CH3:10])[CH3:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[C:8]([C:12]1[CH:17]=[C:16]([N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=[O:7])[CH:15]=[C:14]([I:19])[C:13]=1[O:20][CH3:21])([CH3:11])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 574194401-(Tert-butyl)-3,5-diiodo-2-methoxybenzeneHCID 178516071HCID 178516071, compound

Product 1

HCID 668338521-(3-tert-butyl-5-iodo-4-methoxyphenyl)pyridin-2(1H)-one

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

In a 20 mL microwave tube were added pyridin-2-ol (190 mg, 2 mmol), copper(I) iodide (76 mg, 0.400 mmol), 1-tert-butyl-3,5-diiodo-2-methoxybenzene (998 mg, 2.400 mmol), potassium phosphate (849 mg, 4.00 mmol) and N,N′-dimethylethylenediamine (0.086 mL, 0.800 mmol) in dioxane (10 mL). The tube was sealed and the mixture was sparged with N2 for 10 minutes and heated in an oil bath at 110° C. for 16 hours. The mixture was cooled and partitioned into ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and the filtrate was treated with 3-mercaptopropyl functionalized silica gel, filtered through diatomaceous earth and concentrated in vacuo to give crude product which was purified on an Isco 12 g silica cartridge eluting with 3:2 hexane/ethyl acetate to give the title compound.

Workup

  1. customThe tube was sealed
  2. customthe mixture was sparged with N2 for 10 minutes
  3. temperatureThe mixture was cooled
  4. custompartitioned into ethyl acetate
  5. washThe organic layer was washed with saturated NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. additionthe filtrate was treated with 3-mercaptopropyl functionalized silica gel
  9. filtrationfiltered through diatomaceous earth
  10. concentrationconcentrated in vacuo
  11. customto give crude product which
  12. customwas purified on an Isco 12 g silica cartridge
  13. washeluting with 3:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-897e5be804b745c5ae709807e12d8ec6
Source dataset
uspto-grants-2016_05
Patent number
US09353091B2

Reaction notes

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