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22nd August 2013 @ 13:30

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Reaction information

*#Reaction file  
*Reaction file type CDX

General procedure B (see below) with N-(2-hex-1-ynylphenyl)-4-methyl-benzenesulfonamide (1.64 g, 5.0 mmol) and 1-Bromohex-1-yne (805 mg, 5.0 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave an inseparable 3.3:1 mixture of the title compound and 2‑butyl‑1‑tosyl‑1H-indole(116b) as a yellow oil (1.69 g, 87%).



General procedure B:

A solution of the appropriate bromide (1 eq.) and N,N‑dimethylethylenediamine (0.2 eq.) in dry toluene (20 mL) was added to the appropriate sulfonamide (1 eq.), K3PO4 (2 eq.) and CuI (0.05 eq.) in toluene (10.0 mL).  The reaction mixture was heated to reflux for 16 h.  The reaction mixture was filtered through a plug of silica using ether to elute and the solvent removed in vacuo to give the crude product, which was purified as described.

*Yield (%)  87
*Type of Yield Isolated product yield
AH Thesis_2011_pp88.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 110b: N-(Hex-1-yn-1-yl)-N-(2-(hex-1-yn-1-yl)phenyl)-4-methylbenzenesulfonamide

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp88.pdf
AH Thesis_2011_pp176-223.pdf