Triethylamine → 1-(7-Trimethylsilylacetylenyl-2-benzothiazolyl)-3-ethylurea

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Reaction Conditions

Reaction Steps

A mixture of 1-(7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.080 g, 80% pure, 0.17 mmol), Pd(PPh3)2Cl2 (0.010 g, 0.014 mmol, 0.08 eq), and triethylamine (0.102 mL, 0.73 mmol, 4.3 eq) in 1 mL of anhydrous DMF was bubbled with nitrogen gas for 5 minutes, followed by the addition of trimethylsilyl acetylene (0.12 mL, 0.85 mmol, 5.0 eq). The mixture was heated at about 100° C. with stirring in a sealed tube for about 18 hours. The mixture was cooled down, taken up in 10 mL MeOH, and evaporated to dryness. Purification by flash chromatography on SiO2 with ethyl acetate and heptane (2/1) gave pure desired compound 0.050 g (93%). LC/MS 318 (M+1); LC retention time 9.25 min.

Provenance & Evidence