N-Iodosuccinimide → 2-(4-Ethoxy-phenyl)-3-iodo-pyrazolo[1,5-b]pyridazine

HRID 982641Notes

Reaction equation

HRID 982641 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18](C(O)=O)=[C:17]3[N:12]([N:13]=[CH:14][CH:15]=[CH:16]3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2].[I:22]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]([I:22])=[C:17]3[N:12]([N:13]=[CH:14][CH:15]=[CH:16]3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 120273N-Iodosuccinimide2×HCID 516892Sodium BicarbonateHCID 225623382-(4-ethoxy-phenyl)-pyrazolo[1,5-b]pyridazine-3-carboxylic Acid

Product 1

HCID 225623392-(4-Ethoxy-phenyl)-3-iodo-pyrazolo[1,5-b]pyridazineYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-ethoxy-phenyl)-pyrazolo[1,5-b]pyridazine-3-carboxylic acid (710 mg), N-iodosuccinimide (678 mg) and sodium bicarbonate (717 mg) in DMF (8 ml) was stirred for 4 h. A further quantity of N-iodosuccinimide(100 mg) was added and stirring continued for 2 h. Aqueous workup gave a dark brown solid which was purified by SPE with dichloromethane as eluant. This gave the title compound as an orange-brown solid (429 mg, 47%).

Workup

  1. stirringstirring
  2. waitcontinued for 2 h
  3. customAqueous workup gave a dark brown solid which
  4. customwas purified by SPE with dichloromethane as eluant

Sources & evidence

ORD record
ord-66cf4eb0dfaa428bbad37a15fcc187bc
Source dataset
uspto-grants-2005_03
Patent number
US06861429B2

Reaction notes

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