反应详情

温度

120 °C

A mixture of 6-fluoro-2,3′-bipyridin-5-ylboronic acid (555 mg, 2.55 mmol), 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (700 mg, 1.819 mmol), Amphos 2 (64.4 mg, 0.091 mmol) (Aldrich) and potassium acetate (548 mg, 5.58 mmol) (Aldrich) in dioxane (12 mL) and water (3.0 mL) was purged with argon and heated in a microwave reactor at 120° C. for 30 min. The reaction mixture was treated with 1 N NaOH (15 mL) and extracted with EtOAc (50 mL), washed with brine and dried over MgSO4, filtered and concentrated. The crude product was purified on the ISCO (40 g column, 40-100% EtOAc in hexanes) to give 4-(6-fluoro-2,3′-bipyridin-5-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (490.3 mg, 0.938 mmol, 51.6% yield) as a bright yellow crystalline solid. m/z (ESI, +ve ion) 523.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 9.26 (1H, d, J=1.8 Hz); 8.67-8.72 (2H, m); 8.40 (1H, dt, J=8.0, 2.0 Hz); 7.77 (1H, dd, J=7.8, 1.6 Hz); 7.43 (1H, dd, J=8.0, 5.3 Hz); 7.20-7.25 (4H, m); 6.83-6.90 (4H, m); 4.83 (4H, s); 3.82 (3H, s); 3.80 (3H, s); 2.56 (3H, s).

1. customwas purged with argon
2. additionThe reaction mixture was treated with 1 N NaOH (15 mL)
3. extractionextracted with EtOAc (50 mL)
4. washwashed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified on the ISCO (40 g column, 40-100% EtOAc in hexanes)