Potassium Carbonate → HCID 90387451, compound

HRID 2205218Notes

Reaction equation

HRID 2205218 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.Br[C:12]1[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[K+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:12]3[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 784285-Bromothiophene-2-carbaldehydeHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 517044Potassium Acetate

Product 1

HCID 90387451HCID 90387451, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 6-chloroimidazo[1,2-b]pyridazine (1.55 g, 10.1 mmol, 1.0 equiv) in toluene (10.0 mL) was added 5-bromothiophene-2-carbaldehyde (1.80 mL, 15.1 mmol, 1.5 equiv), potassium carbonate (2.79 g, 20.2 mmol, 2.0 equiv), triphenyl phosphine (529 mg, 2.02 mmol, 0.2 equiv) and potassium acetate (227 mg, 1.01 mmol, 0.1 equiv). The reaction mixture was heated to reflux for 24 h then diluted with water and extracted with ethyl acetate. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 1.60 g of the white solid, 60%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. extractionextracted with ethyl acetate
  4. customPurification by column chromatography
  5. wash50% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-4a7b4db8e8334d94afe8bacbf3dbbd82
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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