1,4-Dioxane → HCID 86631782, compound

HRID 2048152Notes

Reaction equation

HRID 2048152 reaction equation
Br[C:2]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[N:4][C:3]=1[C:10]1[CH:17]=[CH:16][C:13](C=O)=[CH:12][CH:11]=1.C([Sn](CCCC)(CCCC)[C:23]1[S:24][CH:25]=[CH:26][N:27]=1)CCC.[O:36]1CCOC[CH2:37]1>C(Cl)Cl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:24]1[CH:25]=[CH:26][N:27]=[C:23]1[C:2]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[N:4][C:3]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:16][C:17]=1[CH:37]=[O:36]

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 86631783HCID 86631783, compound

Product 1

HCID 86631782HCID 86631782, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-(5-Bromo-imidazo[2,1-b]thiazol-6-yl)-benzaldehyde 0.09 g (0.37 mM) is dissolved in 5 mL of 1,4 dioxane and 0.5 eq of Pd(PPh3)4 is added followed by the addition of 2-(tributylstannyl)-1,3-thiazole (1.1 eq) and the reaction mixture is heated to reflux for 24 h. The reaction mixture is cooled down to room temperature and diluted with 10 mL of methylene chloride and 15 mL of water. The separated organic layer is washed with water and dried over Na2SO4. The crude reaction mixture is used for next step.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 24 h
  3. washThe separated organic layer is washed with water
  4. dry with materialdried over Na2SO4
  5. customThe crude reaction mixture

Sources & evidence

ORD record
ord-a56b9bacc72f43e6aa26fa54f0a88ef8
Source dataset
uspto-grants-2013_11
Patent number
US08592591B2

Reaction notes

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