N-Iodosuccinimide → [1-(3-Iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

HRID 2036656Notes

Reaction equation

HRID 2036656 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[CH:21]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:23]N1C(=O)CCC1=O>C(#N)C.O>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[C:21]=1[I:23])[CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 67433032(1-Imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester

Product 1

HCID 67433097[1-(3-Iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (1-imidazo[1,2-b]pyridazin-2-yl-ethyl)-carbamic acid benzyl ester (2.5 g, 8.44 mmol) in acetonitrile (30 mL) was added N-iodosuccinimide (2.3 g, 10.13 mmol) at rt and stirred overnight. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with satd. sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-5% MeOH in DCM to provide [1-(3-iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester: LC-MS (ESI) m/z 422.9 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialsodium bicarbonate, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-4538b214207f46c39db986138874f505
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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