Stannane, tributyl(1-ethoxyethenyl)- → 6-[6-(1-Ethoxy-vinyl)[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinoline

Participants

Reaction Steps

To a degassed solution of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quino-line (2.50 g, 5.86 mmol) in DMF (20 mL), was added Pd(Ph3P)4 (0.542 g, 0.469 mmol) and the solution was stirred for 20 min at room temperature. Then tributyl(1-ethoxyvinyl)stannane (2.117 g, 5.86 mmol) was added. The reaction was heated to 100° C. until LC-MS showed the reaction was complete. The reaction mixture was filtered through celite and the filtrate was washed with water, dried over Na2SO4, and concentrated. The resulting crude product was purified by silica gel column chromatography with gradient Hex:EA to give 6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (1.2 g, 62%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.19 (s, 1H), 8.94 (m, 1H), 8.20 (m, 1H), 7.99 (s, 1H), 7.89 (d, 1H), 7.548 (m, 1H), 6.12 (s, 2H), 5.61 (d, 1H), 4.61 (d, 1H), 4.05 (q, 2H), 1.51 (t, 3H). LCMS (method B): [MH]+=360, tR=2.40 min.

Provenance & Evidence