Potassium Fluoride → HCID 58516244, compound

HRID 1919174Notes

Reaction equation

HRID 1919174 reaction equation
C([Sn](CCCC)(CCCC)[C:6]([O:8][CH2:9][CH3:10])=[CH2:7])CCC.Br[C:20]1[S:24][C:23]([C:25]2[S:26][C:27](Br)=[CH:28][N:29]=2)=[N:22][CH:21]=1.[F-].[K+]>CN(C)C=O.CCOCC.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>[CH2:9]([O:8][C:6]([C:20]1[S:24][C:23]([C:25]2[S:26][C:27]([C:6]([O:8][CH2:9][CH3:10])=[CH2:7])=[CH:28][N:29]=2)=[N:22][CH:21]=1)=[CH2:7])[CH3:10]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 18791071HCID 18791071, compound

Product 1

HCID 58516244HCID 58516244, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Tributyl(1-ethoxyvinyl)tin (0.425 mL, 1.26 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (21.5 mg, 0.031 mmol) were added to a stirred solution of 5,5′-dibromo-2,2′-bithiazole (200 mg, 0.613 mmol) in dimethylformamide (4 mL) under nitrogen. The reaction mixture was heated at 100° C. for 2 h. The reaction was cooled, diluted with ether and aqueous potassium fluoride (0.5 g in 5 mL of water). The mixture was vigorously stirred for 1 h at room temperature, both phases were filtered through CELITE® and then separated. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (0 to 30% ethyl acetate in hexanes) to yield 5,5′-bis(1-ethoxyvinyl)-2,2′-bithiazole (181 mg, 0.587 mmol, 96% yield) as a yellow solid.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationboth phases were filtered through CELITE®
  3. customseparated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (0 to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fd6a07aaa6a54e988e22206d5da9db94
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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