Reacción #1616565

Ecuación de reacción

3,5-bis(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indole

NaOH

NaCl

→

title compound

Rendimiento 50.0%

3,5-bis(6-cyclopropyl-2-pyrazinyl)-1H-indole

Rendimiento 50.0%

Disolventes

EtOAc

—

hexanes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA glass microwave reaction vessel
2. 2
   Extracciónthe mixture was extracted with EtOAc (3×)
3. 3
   SecadoThe combined organic layers were dried over anhydrous Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe crude product was purified by silica gel chromatography

Procedimiento

A glass microwave reaction vessel was charged with 3,5-bis(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indole (72 mg, 0.14 mmol) and 1 M NaOH (aq., 0.71 mL, 0.71 mmol) in dioxane (1.5 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 20 min. Saturated NaCl (aq.) was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0-70% EtOAc in hexanes, to the title compound (25 mg, 0.07 mmol, 50% yield) as a light-yellow solid. MS (ESI, pos. ion) m/z: 354.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.90 (s, 1H), 9.07-9.14 (m, 1H), 8.95 (d, J=6.46 Hz, 2H), 8.53 (s, 1H), 8.37 (d, J=3.91 Hz, 2H), 7.89-7.97 (m, 1H), 7.60 (s, 1H), 2.22-2.33 (m, 2H), 1.06-1.26 (m, 8H).

Fuente