Potassium Carbonate → HCID 58857869, compound

HRID 2205202Notes

Reaction equation

HRID 2205202 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][CH:19]=[CH:20][C:14]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:16]1[C:12]([C:8]2[N:6]3[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)=[CH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]1=2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 947862-Bromobenzo(b)thiopheneHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-

Product 1

HCID 58857869HCID 58857869, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 6-chloroimidazo[1,2-b]pyridazine (1.59 g, 10.3 mmol, 1.1 equiv) in 28.0 mL of toluene was added 2-bromobenzo[b]thiophene (2.00 g, 9.38 mmol, 1.0 equiv), potassium carbonate (2.59 g, 18.8 mmol, 2.0 equiv), triphenylphosphine (592 mg, 1.88 mmol, 0.2 equiv) and palladium acetate (211 mg, 0.938 mmol, 0.1 equiv). The solution was stirred to reflux for 24 h. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 1.50 g of the yellow solid, 56%.

Workup

  1. temperatureto reflux for 24 h
  2. customPurification by column chromatography
  3. wash50% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-7ed2cf46f541417fb566f407ace6a2c0
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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