Iodine → Ethyl [7-(3-chlorophenyl)-6-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate

HRID 2284457Notes

Reaction equation

HRID 2284457 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[O:16])[NH:14][CH2:13][CH:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:11]3[CH:23]=2)[CH:5]=[CH:6][CH:7]=1.[I:24]I>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[O:16])[NH:14][CH2:13][CH:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:11]3[C:23]=2[I:24])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 807IodineHCID 86731547Ethyl [7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate

Product 1

HCID 86731554Ethyl [7-(3-chlorophenyl)-6-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetateYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl [7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate (280 mg, 0.84 mmol) was dissolved in DCM, cooled in an ice bath and CF3COOAg (186 mg, 0.84 mmol) and Iodine (214 mg, 0.84 mmol) were added. The reaction was then warmed up at room temperature and after 1 hour was complete. It was filtered through paper, evaporated and the crude purified by silica chromatography (eluent: Hexane/AcOEt 3/2) to give 228 mg of desired product (59% yield).

Workup

  1. temperaturecooled in an ice bath
  2. filtrationIt was filtered through paper
  3. customevaporated
  4. customthe crude purified by silica chromatography (eluent: Hexane/AcOEt 3/2)

Sources & evidence

ORD record
ord-be8d772ab2164137afd4bf1f29b2e695
Source dataset
uspto-grants-2015_09
Patent number
US09145418B2

Reaction notes

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