Potassium Iodide → HCID 58577728, compound

HRID 587430Notes

Reaction equation

HRID 587430 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]1=[O:10].Br[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.CNCCNC.[I-].[K+]>O1CCOCC1.[Cu]I>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[CH2:3][C:2]2=[O:10])=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8070N,N'-DimethylethylenediamineHCID 114661-Bromo-4-nitrobenzeneHCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 58577728HCID 58577728, compoundYield 25.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
95 °C

Procedure

A mixture of 1H-pyrrolo[2,3-b]pyridin-2(3H)-one (431 mg), 1-bromo-4-nitrobenzene (778 mg), copper(I) iodide (122 mg), N1,N2-dimethylethane-1,2-diamine (113 mg) and potassium iodide (1.36 g) in 1,4-dioxane (10 mL) was sparged with argon for 5 min then heated overnight at 95° C. After this time, the reaction mixture was cooled to ambient temperature, diluted with ethyl acetate (100 mL), filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, heptane to 1:1 ethyl acetate/heptane) to afford 1-(4-nitrophenyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (207 mg) as a white solid.

Workup

  1. customwas sparged with argon for 5 min
  2. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
  3. additiondiluted with ethyl acetate (100 mL)
  4. filtrationfiltered through diatomaceous earth
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by chromatography (silica, heptane to 1:1 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-8dd84eeae2b84cfa9daae56bd60233b9
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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