Tetrabutylammonium Fluoride → 2-(1H-Pyrrol-3-yl)-1,3-thiazole

HRID 746827Notes

Reaction equation

HRID 746827 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6]1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH:5]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 693030142-{1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}-1,3-thiazole

Product 1

HCID 1362498942-(1H-Pyrrol-3-yl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]-1,3-thiazole (200 mg, 0.65 mmol) in 2 mL THF was added dropwise tetrabutylammonium fluoride (0.98 mL of 1M in THF, 0.98 mmol), after 20 minute the reaction was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica gel using an ISCO single channel system (Hexane/EtOAc=9/1 to 1/9) to afford 2-(1H-pyrrol-3-yl)-1,3-thiazole as a yellow oil.

Workup

  1. customafter 20 minute the reaction was quenched with H2O (30 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude purified by liquid chromatography on silica gel using an ISCO single channel system (Hexane/EtOAc=9/1 to 1/9)

Sources & evidence

ORD record
ord-49a9dd45f881499da3040d2b0b871ffb
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

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