反应详情

温度

100 °C

A mixture of 2-chloro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (500 mg, 1.97 mmol), 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) (125 mg, 0.20 mmol), palladium(II) acetate (22 mg, 0.10 mmol), potassium carbonate (413 mg, 2.96 mmol), and methanol (1.20 mL, 29.59 mmol) in DMF (6 mL) was evacuated and then filled with nitrogen (3×), and then evacuated and filled with carbon monoxide (2×). The reaction mixture was then heated at 100° C. for 2 hours under a balloon of carbon monoxide. The cooled reaction was diluted with ethyl acetate (10 mL), filtered over Celite, and concentrated in vacuo to provide a dark red residue that was filtered through a silica plug, eluting with ethyl acetate (60 mL). The pale yellow eluent was concentrated in vacuo to afford the title compound as a yellow oil (350 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.91 (s, 1H), 4.00 (s, 3H), 2.59 (s, 3H), 1.36 (s, 12H).

1. customwas evacuated
2. additionfilled with nitrogen (3×)
3. customevacuated
4. additionfilled with carbon monoxide (2×)
5. customThe cooled reaction
6. filtrationfiltered over Celite
7. concentrationconcentrated in vacuo
8. customto provide a dark red residue that
9. filtrationwas filtered through a silica plug
10. washeluting with ethyl acetate (60 mL)
11. concentrationThe pale yellow eluent was concentrated in vacuo