Tert-butyl 2-iodobenzoate → t-Butyl 2-[4-[(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)methyl]phenyl]benzoate

HRID 1655526Notes

Reaction equation

HRID 1655526 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Sn](C)(C)C)=[CH:17][CH:16]=1)[CH3:2].I[C:26]1[CH:38]=[CH:37][CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:26][C:27]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:17][CH:16]=1)[CH3:2]

Participants

5

Reactant 2

HCID 11438134Tert-butyl 2-iodobenzoateHCID 197841424-[(2-Ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)methyl]phenyltrimethylstannane

Product 1

HCID 19784151t-Butyl 2-[4-[(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)methyl]phenyl]benzoateYield 73%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.149 g (0.35 mmol) of the product of Step G and 0.132 g (0.43 mmol) of t-butyl 2-iodobenzoate in 1 mL of anhydrous DMF was added 5 mg of bis(triphenylphosphine)palladium(II) chloride. The mixture was degassed, flushed with nitrogen, then magnetically stirred under a nitrogen atmosphere for 12 hours at 100° C. The reaction mixture was cooled to room temperature, then partitioned between EtOAc and water. The organic layer was extracted, separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 50% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.111 g (73%) of the title compound as an off-white amorphous solid.

Workup

  1. customThe mixture was degassed
  2. customflushed with nitrogen
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between EtOAc and water
  5. extractionThe organic layer was extracted
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 50% EtOAc-hexane
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-904b5b14ddf64470a58787b61e8a0253
Source dataset
uspto-grants-1993_10
Patent number
US05250521

Reaction notes

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