Reacción #1102146

Ecuación de reacción

triethylamine

2-chlorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

2-iodoadenosine

→

product

(3-[1-((2-Chloro)phenoxycarbanoyl)piperidin-4-yl]propyn-1-yl}adenosine

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued a further 72 h
4. 4
   FiltraciónThe suspension was filtered through celite
5. 5
   Otrothe resulting solution evaporated to dryness
6. 6
   OtroThe crude was purified by column chromatography
7. 7
   Lavadoeluting with a gradient of DCM/MeOH (0-4%)

Procedimiento

To a solution of 2-iodoadenosine (0.602 g, 1.531 mmol) in freshly degassed DMF (20 mL) was added degassed triethylamine (1.20 mL, 8.54 mmol), Pd(PPh3)4 (85 mg, 0.074 mmol), CuI (catalytic), and 2-chlorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate (0.588 g, 2.117 mmol). The mixture was stirred at room temperature under and inert atmosphere for 20 h. Silica bound Pd(II) scavenger Si-thiol (400 mg) and Pd(0) scavenger Si-TAAcOH (619 mg) were added and stirring continued a further 72 h. The suspension was filtered through celite and the resulting solution evaporated to dryness. The crude was purified by column chromatography, eluting with a gradient of DCM/MeOH (0-4%) to afford the pure product as a white solid: yield 0.733 g, 88%.

Fuente