Piperidine → HCID 22998462, compound

HRID 1166966Notes

Reaction equation

HRID 1166966 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH3:15][C:16]([CH3:20])([CH3:19])[C:17]#[CH:18].N1CCCCC1>O.[Cu](I)I>[CH3:15][C:16]([CH3:20])([CH3:19])[C:17]#[C:18][C:2]1[S:6][C:5]([S:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 135123,3-Dimethyl-1-butyneHCID 23445587N-(5-bromothiophenesulfonyl)pyrrole

Product 1

HCID 22998462HCID 22998462, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Procedure

A mixture of N-(5-bromothiophene-2-sulfonyl)pyrrole (600 mg, 2.05 mmol), 3,3-dimethyl-1-butyne (338 mg, 4.1 mmol), copper iodide (39 mg, 0.21 mmol), tetrakistriphenylphosphine palladium[Pd(PPh3)4] (118 mg, 0.1 mmol) and piperidine (5 ml) was stirred at room temperature for a period of 24 hours under a nitrogen atmosphere. The mixture was then diluted with water (10 ml) and extracted with 3×25 ml portions of ether. The combined ether extracts are washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and crude product purified by column chromatography using 2% ethyl acetate/hexanes to give 423 mg N-[5-(3,3-dimethylbutyn-1-yl)thiophene-2-sulfonyl]pyrrole as a yellow powder (70% yield).

Workup

  1. extractionextracted with 3×25 ml portions of ether
  2. washThe combined ether extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure and crude product
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-02f578ed68b245a280154268266cb53e
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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