Reacción #2292792

Ecuación de reacción

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

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

K2CO3

→

title compound

Rendimiento 87.0%

tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Rendimiento 87.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter the solvent was removed
2. 2
   Otrothe residue was purified by silica gel column chromatography (PE/EtOAc=7:1)

Procedimiento

A mixture of benzyl (S)-(1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (850 mg, 2.19 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (904 mg, 3.06 mmol), K2CO3 (605 mg, 4.38 mmol) and Pd(dppf)Cl2 (170 mg, 0.22 mmol) in anhydrous DMF (25 mL) was stirred at 100° C. for 5 hours under nitrogen. After the solvent was removed, the residue was purified by silica gel column chromatography (PE/EtOAc=7:1) to give the title compound as a yellow oil (900 mg, 87%). ESI-MS m/z [M+H]+ calc'd for C22H32N4O4, 477. found 477.

Fuente