Potassium Carbonate → HCID 57418688, compound

HRID 2205222Notes

Reaction equation

HRID 2205222 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[CH:16]=[CH:15][S: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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 133833-BromothiopheneHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 517044Potassium Acetate

Product 1

HCID 57418688HCID 57418688, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-chloroimidazo[1,2-b]pyridazine (200 mg, 1.30 mmol, 1.0 equiv) in toluene (5.00 mL) was added 3-bromothiophene (0.18 mL, 1.95 mmol, 1.5 equiv), potassium carbonate (360 mg, 2.60 mmol, 2.0 equiv), triphenyl phosphine (68 mg, 0.260 mmol, 0.20 equiv) and potassium acetate (29 mg, 0.130 mmol, 0.1 equiv). The reaction mixture was heated to reflux for 24 h. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 201 mg of the white solid, 85%.

Workup

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

Sources & evidence

ORD record
ord-9b812d3e96204778bbea439d48a122ff
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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