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

HRID 982638Notes

Reaction equation

HRID 982638 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-3e8dc375ddd24c0e93c6a133d49e67e1
Source dataset
uspto-grants-2005_03
Patent number
US06861429B2

Reaction notes

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