Hexane → HCID 57933094, compound

HRID 1432729Notes

Reaction equation

HRID 1432729 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.C([Li])CCC.CCCCCC.Br[C:19]1[S:20][C:21]([C:28]2[N:32]3[N:33]=[C:34]([CH3:42])[CH:35]=[C:36]([CH:37]([CH2:40][CH3:41])[CH2:38][CH3:39])[C:31]3=[N:30][C:29]=2[CH3:43])=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=1.[NH4+].[Cl-]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH2:38]([CH:37]([C:36]1[C:31]2[N:32]([C:28]([C:21]3[S:20][C:19]([C:6]4[N:2]([CH3:1])[N:3]=[CH:4][N:5]=4)=[N:23][C:22]=3[C:24]([F:25])([F:26])[F:27])=[C:29]([CH3:43])[N:30]=2)[N:33]=[C:34]([CH3:42])[CH:35]=1)[CH2:40][CH3:41])[CH3:39]

Participants

8

Reactant 5

HCID 8058HexaneHCID 224591H-1,2,4-Triazole, 1-methyl-HCID 25517Ammonium ChlorideHCID 68840477HCID 68840477, compoundHCID 178418339Butyllithium

Product 1

HCID 57933094HCID 57933094, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

164 mg of 1-Methyl-1,2,4-triazole (1.96 mmol) is dissolved in 2 ml of THF and cooled to −78° C. 0.8 ml of 2.5M n-butyllithium in hexane (1.96 mmol) is added slowly and stirred at −78° C., warmed up to room temperature and stirred at r.t. for 15 min and cooled to −78° C. 3.96 ml of 0.5 M ZnCl2 in THF (1.98 mmol) is added and stirred at room temperature for 15 min. 180 mg of 3-(2-bromo-4-trifluoromethyl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine and 54 mg of PdCl2(pddf) (0.06 mmol) are added. The vial is capped with a Teflon cap and heated at 80° C. overnight. NH4Cl aq. is added to quench the reaction and the mixture is extracted by CH2Cl2, dried over Na2SO4 and evaporated. The crude product is applied onto silica-gel chromatography column (Hexane:AcOEt=3:1) to give 119 mg of the title compound. Yield 58%. mass spectrum (m/e): 449 (M+1).

Workup

  1. temperaturewarmed up to room temperature
  2. stirringstirred at r.t. for 15 min
  3. temperaturecooled to −78° C
  4. stirringstirred at room temperature for 15 min
  5. customcap
  6. temperatureheated at 80° C. overnight
  7. customto quench
  8. customthe reaction
  9. extractionthe mixture is extracted by CH2Cl2
  10. dry with materialdried over Na2SO4
  11. customevaporated

Sources & evidence

ORD record
ord-5135ea6820604e21a22c52e5bd8cb064
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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