Iodoethane → 2-(4-Ethoxyphenyl)-3-[4-(methylsulfonyl)phenyl]pyrazolo[1,5-b]pyridazine

HRID 1280404Notes

Reaction equation

HRID 1280404 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[N:13][N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[N:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].I[CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:28]([O:26][C:23]1[CH:22]=[CH:21][C:20]([C:12]2[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=3)=[C:19]3[N:14]([N:15]=[CH:16][CH:17]=[CH:18]3)[N:13]=2)=[CH:25][CH:24]=1)[CH3:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 135405232HCID 135405232, compound

Product 1

HCID 98326872-(4-Ethoxyphenyl)-3-[4-(methylsulfonyl)phenyl]pyrazolo[1,5-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[3-(4-Methanesulfonyl-phenyl)-pyrazolo[1,5-b]pyridazin-2-yl]-phenol (663 mg, 1.82), iodoethane (1 eq) and potassium carbonate (2 eq) in acetonitrile (30 ml) were heated at reflux under nitrogen for 18 h. The cooled reaction mixture was partitioned between water (30 ml) and ethyl acetate (30 ml). The organic phase was collected, dried and purified by chromatography to give the title compound (547 mg) as a cream foam.

Workup

  1. temperatureat reflux under nitrogen for 18 h
  2. customThe cooled reaction mixture
  3. customwas partitioned between water (30 ml) and ethyl acetate (30 ml)
  4. customThe organic phase was collected
  5. customdried
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-86d2345cfac145f8804dccad58502abe
Source dataset
uspto-grants-2002_09
Patent number
US06451794B1

Reaction notes

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