Reaction #321634

Reaction equation

N-(5-bromothiophene-2-sulfonyl)pyrrole

3,3-dimethyl-1-butyne

piperidine

→

N-[5-(3,3-dimethylbutyn-1-yl)thiophene-2-sulfonyl]pyrrole

Yield 70.3%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with 3×25 ml portions of ether
2. 2
   WashThe combined ether extracts are washed with brine
3. 3
   Dryingdried over MgSO4
4. 4
   OtherThe solvent was removed under reduced pressure and crude product
5. 5
   Otherpurified by column chromatography

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).

Source