Hydrochloric Acid → HCID 135405232, compound

HRID 1280403Notes

Reaction equation

HRID 1280403 reaction equation
B(Br)(Br)Br.[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:24]3[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=3)=[N:17][N:18]3[C:23]=2[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:11][CH:10]=1)(=[O:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].Cl>C(Cl)Cl.O>[CH3:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)=[N:17][N:18]3[C:23]=2[CH:22]=[CH:21][CH:20]=[N:19]3)=[CH:13][CH:14]=1)(=[O:7])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 11440364HCID 11440364, compound

Product 1

HCID 135405232HCID 135405232, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M solution in CH2Cl2, 2.1 eq) was added to 3-(4-methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-pyrazolo[1,5-b]pyridazine (3.58 g) in CH2Cl2 at −70°. The mixture was stirred for 10 min then warmed to 0° and stirred at 0° overnight. The reaction mixture was made alkaline with potassium carbonate then acidified with hydrochloric acid (2M), poured into water and extracted into CH2Cl2. The organic phase was dried, filtered and concentrated to give the title compound (1.87 g) as a yellow solid.

Workup

  1. temperaturethen warmed to 0°
  2. stirringstirred at 0° overnight
  3. extractionextracted into CH2Cl2
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9e11199d2aaf479fa2c0680235749b11
Source dataset
uspto-grants-2002_09
Patent number
US06451794B1

Reaction notes

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