Reacción #73448

Ecuación de reacción

DCM

(4-chloropyridin-2-yl)methanol

1H-indol-5-ol

cesium carbonate

→

title compound

(4-(1H-indol-5-yloxy)pyridin-2-yl)methanol

Disolventes

brine

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction is sealed
2. 2
   TemperaturaThe reaction mixture is then cooled to room temperature
3. 3
   OtroThe resulting layers are separated
4. 4
   Extracciónthe aqueous layer is extracted three additional times with DCM
5. 5
   SecadoThe organic layers are combined dried over anhydrous Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe resulting residue is purified via FCC (0-100% EtOAc/heptane)

Procedimiento

To a solution of (4-chloropyridin-2-yl)methanol (384 mg, 2.67 mmol) in DMF (12 mL) is added 1H-indol-5-ol (534 mg, 4.01 mmol), and cesium carbonate (1307 mg, 4.01 mmol). The reaction is sealed and heated to 160° C. via microwave irradiation for 30 min. The reaction mixture is then cooled to room temperature and diluted brine and DCM. The resulting layers are separated and the aqueous layer is extracted three additional times with DCM. The organic layers are combined dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue is purified via FCC (0-100% EtOAc/heptane) to give the title compound. MS (ESI) m/z 241.2 (M+1).

Fuente