Thiazole → HCID 68629712, compound

HRID 1855382Notes

Reaction equation

HRID 1855382 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].C([O-])(=O)C.[K+].[S:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>CC(N(C)C)=O.C(OCC)(=O)C.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>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:22]1[S:18][CH:19]=[N:20][CH:21]=1

Participants

8

Reactant 3

HCID 9256ThiazoleHCID 1012932-Bromo-5-nitroanisoleHCID 517044Potassium Acetate

Product 1

HCID 68629712HCID 68629712, compoundYield 59%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

In a microwave vial, a mixture of 2-bromo-5-nitroanisole (300 mg, 1.27 mmol), potassium acetate (188 mg, 1.90 mmol) and tetrakis(triphenylphosphine)palladium(0) (74 mg, 0.634 mmol) in 4 ml dimethyl acetamide was flushed with argon. Thiazole (459 uL, 6.34 mmol) was added, the tube was sealed, and the mixture was heated for 1 h to 160° C. in a microwave oven. The mixture was diluted with ethyl acetate and water, the layers were separated and the aqueous layer was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure. The residual material was subjected to column chromatography on silica gel using heptane/ethyl acetate (7:3) as eluent to afford the title compound as yellow solid (177 mg, 59%). Mp 125-128° C.

Workup

  1. customwas flushed with argon
  2. customthe tube was sealed
  3. temperaturethe mixture was heated for 1 h to 160° C. in a microwave oven
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-93c9ce8ca0704bea878630a53a38016c
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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