Reacción #313217

Ecuación de reacción

2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

1-methyl-1H-pyrrolo[2,3-b]pyridine

THF

n-Bu—Li

→

title compound

Rendimiento 11.0%

1-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Rendimiento 11.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution is heated to
2. 2
   Temperaturaa reflux for 1 hour
3. 3
   Lavadowashed with water (2×100 mL), brine (75 mL)
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue is purified by ISCO (5%-15% EtOAc gradient)

Procedimiento

To a −78° C. solution of 1-methyl-1H-pyrrolo[2,3-b]pyridine (example Rupp-28) (1.17 g, 8.85 mmol) and THF (12 mL) is added 1.6M n-Bu—Li (6.6 mL, 10.62 mmol). The solution is heated to a reflux for 1 hour, cooled to ambient temperature, and 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.60 mL, 17.70 mmol) is added. After 1 hour, the solution is diluted with CH2Cl2 (100 mL), washed with water (2×100 mL), brine (75 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (5%-15% EtOAc gradient) to furnish the title compound (0.25 g, 0.97 mmol, 11%). 1H NMR (CDCl3), δ 1.38 (s, 12H), 4.07 (s, 3H), 7.02 (dd, J=7.9, 4.7 Hz, 1H), 7.07 (s, 1H), 7.92 (d, J=7.9, 1.8 Hz, 1H), 8.39 (d, J=4.7, 1.8 Hz, 1H) ppm. LC/MS (m/z): calcd. for C14H19BN2O2 (M+H)+: 259.2. found: 258.7.

Fuente