Tetrahydrofuran → HCID 86683856, compound

HRID 340454Notes

Reaction equation

HRID 340454 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Br:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([C:31]2[CH:35]=[CH:34][N:33]([Si](C(C)C)(C(C)C)C(C)C)[CH:32]=2)[CH:30]=1>O>[Br:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([C:31]2[CH:35]=[CH:34][NH:33][CH:32]=2)[CH:30]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86683857HCID 86683857, compound

Product 1

HCID 86683856HCID 86683856, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tetrabutylammonium fluoride (1M tetrahydrofuran solution: 1 ml) was added to a tetrahydrofuran (2 ml) solution containing 3-bromo-5-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)pyridine (71 mg), followed by stirring at room temperature for 2 hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5:1 to 2:1), and a white solid of 3-bromo-5-(1H-pyrrol-3-yl)pyridine (28 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5:1 to 2:1)

Sources & evidence

ORD record
ord-06e72751ba3b4dc780e05b23f3622e9a
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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