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

HRID 711402Notes

Reaction equation

HRID 711402 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[N:11]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[CH:14]=[C:10]2[C:9](=[O:22])[NH:8][CH2:7]1)[CH3:2].[I:24]I>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[N:11]2[C:12]([I:24])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[CH:14]=[C:10]2[C:9](=[O:22])[NH:8][CH2:7]1)[CH3:2]

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-804f89834bbe4bd0914b81463ed0f6a2
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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