Potassium Carbonate → HCID 90387518, compound

HRID 2205224Notes

Reaction equation

HRID 2205224 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH3:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.Br[C:14]1[S:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH:15]=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>[S:18]1[C:14]([C:8]2[N:6]3[N:7]=[C:2]([Cl:1])[C:3]([CH3:12])=[C:4]([CH3:11])[C:5]3=[N:10][CH:9]=2)=[CH:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]1=2

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 947862-Bromobenzo(b)thiopheneHCID 517044Potassium AcetateHCID 15271015HCID 15271015, compound

Product 1

HCID 90387518HCID 90387518, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-chloro-7,8-dimethylimidazo[1,2-b]pyridazine (162 mg, 0.892 mmol, 1.0 equiv) in toluene (5.00 mL) was added 2-bromobenzo[b]thiophene (213 mg, 1.16 mmol, 1.3 equiv), potassium carbonate (247 mg, 1.78 mmol, 2.0 equiv), triphenyl phosphine (47 mg, 0.178 mmol, 0.20 equiv) and potassium acetate (20 mg, 0.0892 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 105 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-f16de50bc5b844e4a778e5896c40aec3
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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