反应详情

温度

80 °C

To 5-methoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-ylboronic acid (398 mg, 1.932 mmol) was added sodium carbonate (410 mg, 3.86 mmol), lithium chloride (164 mg, 3.86 mmol), tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (640 mg, 1.932 mmol) and deairared 1,4-Dioxane (15 mL) at rt temperature, followed by tetrakis (triphenylphosphine)pladdinum (0) (112 mg, 0.097 mol), and H2O (1 mL). The resulting light brown mixture was stirred at 80° C. for 2 hr. After cooling down to rt, the mixture was partitioned between H2O/EtOAc (30 mL/50 mL), and separated. The organic layer was washed with brine (10 mL), dried (Na2SO4), concentrated on rotary vacuo, purified on Biotage Flash Collector eluting with 30˜80% EtOAc/Hexanes (1200 mL) to afford the expected product, tert-butyl 4-(5-methoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (207 mg, 32%). 1H-NMR (400 MHz, MeOD) δ ppm 1.44-1.51 (m, 9 H) 2.51 (d, J=1.51 Hz, 2 H) 3.59 (s, 2 H) 3.78 (s, 3 H) 3.93 (s, 3 H) 4.04 (s, 2 H) 4.86 (s, 1 H) 5.82 (s, 1 H) 6.39 (d, J=2.52 Hz, 1 H) 7.27 (d, J=3.27 Hz, 1 H) 7.58 (s, 1 H); Mass spec 344.18 (MH+) Calc for C19H25N3O3 343.19.

1. temperatureAfter cooling down to rt
2. customthe mixture was partitioned between H2O/EtOAc (30 mL/50 mL)
3. customseparated
4. washThe organic layer was washed with brine (10 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated on rotary vacuo
7. custompurified on Biotage Flash Collector
8. washeluting with 30˜80% EtOAc/Hexanes (1200 mL)