Sodium Iodide → 6-Iodo-2-oxindole

HRID 2116786Notes

Reaction equation

HRID 2116786 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Na+].[I-:13].CN[C@@H]1CCCC[C@H]1NC.[NH4+].[OH-]>[Cu]I.O1CCOCC1>[I:13][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14923Ammonium HydroxideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 534188196-Iodo-2-oxindoleYield 84%

Reagents, catalysts & solvents 2

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

Procedure

A schlenk tube and stir bar were dried in an oven overnight and then were evacuated, filled with Ar(g) and cooled. The schlenk tube was charged with CuI (45 mg, 0.236 mmol, 5 mol %), 6-bromoxindole (1.0 g, 4.72 mmol), and NaI (1.42 g, 9.44 mmol). The schlenk tube was evacuated and backfilled with Ar(g) (3 times). Racemic trans-N,N′-dimethyl-1,2-cyclohexanediamine (74 μL, 0.472 mmol, 10 mol %) and anhydrous dioxane (4.72 mL) were added via syringe under Ar(g). The schlenk tube was sealed with a teflon valve and the suspension was stirred at 110° C. for 24 h. The reaction was then cooled to room temperature and 15% NH4OH(aq) (˜50 mL) was added to the reaction mixture while stirring. The suspension was allowed to stir for about 30 min after which the tan solid was vacuum filtered and dried affording 6-Iodooxindole in 84% yield (1.027 g, 3.96 mmol).

Workup

  1. customwere dried in an oven overnight
  2. customwere evacuated
  3. additionfilled with Ar(g)
  4. temperaturecooled
  5. customThe schlenk tube was evacuated
  6. customThe schlenk tube was sealed with a teflon valve
  7. stirringthe suspension was stirred at 110° C. for 24 h
  8. stirringwhile stirring
  9. stirringto stir for about 30 min after which the tan solid
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-1c5d583a7a57496b957b838eaa57ef51
Source dataset
uspto-grants-2008_10
Patent number
US07439371B2

Reaction notes

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