Reacción #162485

Ecuación de reacción

(S)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

cesium carbonate

→

title compound

(S)-tert-Butyl (1-(6-(3,6-dihydro-2H-pyran-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Disolventes

EtOAc

dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with saturated aqueous NH4Cl (3×)
2. 2
   SecadoThe combined organic layers were dried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe product was purified

Procedimiento

To a 20 mL microwave vial were added (S)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (1 g, 2.8 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.890 g, 4.23 mmol), PdCl2(dppf) (0.207 g, 0.282 mmol) and cesium carbonate (1.84 g, 5.65 mmol) in dioxane (12 mL) and water (2 mL). The resulting brown suspension was heated in a microwave reactor at 90° C. on high absorbance for 1 hour. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified using silica gel column chromatography (12 g, 2:8 to 8:2 EtOAc/hexane) to give the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.13 (m, 9 H), 1.25-1.38 (m, 12 H), 3.74-3.97 (m, 7 H), 4.16-4.26 (m, 2H), 4.90-5.05 (m, 1 H), 5.68-5.77 (m, 1 H), 6.47-6.55 (m, 1 H), 6.76-6.87 (m, 1 H), 7.59 (s, 2 H); ESI-MS m/z [M+H]+ calc'd for C20H27N3O3, 358; found 358.

Fuente