2-(Tri-n-butylstannyl)thiophene → 2-(4-Isopropoxyphenoxy)-5-thien-2-yl-1,3,4-thiadiazole

Participants

Reaction Conditions

Reaction Steps

A solution of Example 24C (0.58 g, 1835 mmol) and 2-tributylstannylthiophene (0.816 ml, 2.57 mmol) in DME (15 mL) was degassed by bubbling nitrogen into the reaction mixture via a 20-gauge needle for 10 minutes. PdCl2(PPh3)2 was added and the reaction was heated at reflux under a nitrogen atmosphere for 20 hours. The reaction was cooled to 25° C. and concentrated under reduced pressure on a rotary evaporator to provide 1.6 g of a golden oil. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 1% to 15% ethyl acetate in hexanes to provide 0.51 g (88%) of the title compound as a pale purple oil which crystallized on standing, 1H NMR (300 MHz, DMSO-d6) δ ppm 7.79 (d, J=5.15 Hz, 1H) 7.66 (d, J=3.68 Hz, 1H) 7.40 (d, J=9.19 Hz, 2H) 7.18 (dd, J=5.15, 3.68 Hz, 1H) 7.03 (d, J=9.19 Hz, 2H) 4.64 (heptet, J=5.88 Hz, 1H) 1.28 (d, J=5.88 Hz, 6H); MS (DCI) m/z 319 (M+H)+.

Provenance & Evidence