Potassium Carbonate → HCID 90388487, compound

HRID 2205227Notes

Reaction equation

HRID 2205227 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]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:14]=2[C:13]=1[CH3:22].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[S:16][C:15]4[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:14]=4[C:13]=3[CH3:22])=[CH:9][N:10]=2)[N:7]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 517044Potassium AcetateHCID 27355482-Bromo-5-chloro-3-methylbenzo[b]thiophene

Product 1

HCID 90388487HCID 90388487, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-chloroimidazo[1,2-b]pyridazine (606 mg, 3.95 mmol, 1.0 equiv) in toluene (10.00 mL) was added 2-bromo-5-chloro-3-methylbenzo[b]thiophene (1.03 g, 3.95 mmol, 1.0 equiv), potassium carbonate (1.09 g, 7.90 mmol, 2.0 equiv), triphenyl phosphine (207 mg, 0.790 mmol, 0.20 equiv) and potassium acetate (89 mg, 0.395 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 500 mg of the white solid, 38%.

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-40d3a37ded854ae78b04752c8b5dc50d
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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