N-Iodosuccinimide → 3-Iodo-2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine

HRID 1432677Notes

Reaction equation

HRID 1432677 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])=[CH:8][C:7]([CH3:17])=[N:6][N:5]2[CH:18]=1.C1C(=O)N([I:26])C(=O)C1>C(#N)C>[I:26][C:18]1[N:5]2[N:6]=[C:7]([CH3:17])[CH:8]=[C:9]([CH:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[C:4]2=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 688409972,6-Dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine

Product 1

HCID 579329063-Iodo-2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 50 mL round bottom flask is charged with 2,6-dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine (0.51 g, 0.0021 moles) and acetonitrile (3 mL). The reaction mixture is placed on an ice bath and NIS (0.468 g, 0.00208 moles) is added neat. The reaction is stirred overnight and the ice bath melts. The next day, the reaction mixture is partitioned between dichloromethane and a saturated aqueous solution of NaHCO3. The organic layer is collected and the aqueous layer is extracted two more times with dichloromethane. The organic extracts are combined, washed with brine, and dried over Na2SO4. The solvent is evaporated and the crude material is purified via silica gel chromatography eluting with hexanes and then a 25:75 mixture of ethyl acetate and hexanes. Yield=0.435 g (56%). MS (APCI): 372 (M+1).

Workup

  1. customThe reaction mixture is placed on an ice bath
  2. customThe next day, the reaction mixture is partitioned between dichloromethane
  3. customThe organic layer is collected
  4. extractionthe aqueous layer is extracted two more times with dichloromethane
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent is evaporated
  8. customthe crude material is purified via silica gel chromatography
  9. washeluting with hexanes
  10. additiona 25:75 mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-b19eb155eac84522b3898c832019716f
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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