Ethyl Acetate → HCID 59579876, compound

HRID 2279650Notes

Reaction equation

HRID 2279650 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1)CCC.[F-].[K+].CCOC(C)=O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 132827592-Bromo-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 59579876HCID 59579876, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester (303 mg), 2-tributylstannanyl-pyrimidine (553 mg) and dichlorobis(triphenylphosphine)-palladium (II) (70 mg) in dioxane (5 mL) is heated at 110° C. in a sealed tube overnight. After the reaction mixture is cooled, a potassium fluoride solution and EtOAc are added and the mixture is stirred for 1 h and filtered. The organic layer is separated and aqueous layer is extracted with EtOAc once. The combined extracts are concentrated and the residue is purified by chromatography (silica gel, 4:1 Hexane and EtOAc) to give the title compound.

Workup

  1. temperatureAfter the reaction mixture is cooled
  2. filtrationfiltered
  3. customThe organic layer is separated
  4. extractionaqueous layer is extracted with EtOAc once
  5. concentrationThe combined extracts are concentrated
  6. customthe residue is purified by chromatography (silica gel, 4:1 Hexane and EtOAc)

Sources & evidence

ORD record
ord-ae8bcc6532d840c49027d8df428a923e
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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