Reacción #714643

Ecuación de reacción

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

KOt-Bu

Et3SiH

→

title compound

Rendimiento 73.0%

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

Rendimiento 73.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter aqueous work up, the crude reaction mixture
2. 2
   Otrowas purified by chromatography on silica using step gradient elution (
3. 3
   Temperaturaincreasing the polarity of the eluent stepwise to 30% EtOAc in Hexanes)

Procedimiento

The reaction was conducted according to the General Procedure by heating N-methyl-1H-pyrrolo[2,3-b]pyridine (66 mg, 0.5 mmol, 1 equiv.), KOt-Bu (11 mg, 0.1 mmol, 0.2 equiv.) and Et3SiH (239 microliters, 1.5 mmol, 3 equiv.) in 1 mL of tetrahydrofuran for 45 hours at 35° C. After aqueous work up, the crude reaction mixture was purified by chromatography on silica using step gradient elution (starting with 100% hexanes and increasing the polarity of the eluent stepwise to 30% EtOAc in Hexanes) to obtain 89 mg (73%) of the title compound as a pale yellow oil. 1H NMR (500 MHz, THF-d8) δ 8.45-7.95 (m, 1H), 7.97-7.66 (m, 1H), 6.95 (dd, J=7.7, 4.6 Hz, 1H), 6.68 (s, 1H), 3.94 (s, 2H), 1.05-1.00 (m, 9H), 0.97 (td, J=7.1, 1.7 Hz, 6H). 13C NMR (126 MHz, THF-d8) δ 150.95, 142.87, 137.82, 127.38, 120.13, 114.79, 110.76, 30.27, 6.74, 3.31. HRMS: [C14H23N2Si] calculated 247.1642, measured 247.1631. The HSQC spectrum of this reaction product as provided in FIG. 10.

Fuente