Reacción #169965

Ecuación de reacción

2-bromo-4-fluorobenzonitrile

furan-2-ylboronic acid

Na2CO3

→

title compound

Rendimiento 35.0%

4-Fluoro-2-(furan-2-yl)benzonitrile

Rendimiento 35.0%

Disolventes

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe crude was purified by Combiflash chromatography (24 g column, 8 g silica., gradient of eluent from PE to PE/EtOac 9/1)

Procedimiento

Following the same procedure used for AUP01158-1, AUP01160-1 was prepared from 2-bromo-4-fluorobenzonitrile (5.0 g, 25.0 mmol), furan-2-ylboronic acid (3.36 g, 30.0 mmol), Pd2(dba)3 (100 mg), 1,2-dimethoxyethane (25 mL) and 2M Na2CO3 (40 mL). The crude was purified by Combiflash chromatography (24 g column, 8 g silica., gradient of eluent from PE to PE/EtOac 9/1) to give the title compound as a light yellow solid. This solid had to be purified an ultimate time by drying under vacuum at 40° C. for 5 days. Finally, pure expected compound was obtained as a white off solid in 35% yield (1.65 g); mp 55-56° C.; 1H NMR (270 MHz, CDCl3) δ 6.58-6.59 (1H, m, ArH), 7.02 (1H, td, J=2.7 and 8.0 Hz, ArH), 7.40 (1H, d, J=3.6 Hz, ArH), 7.57 (1H, s, ArH), 7.62 (1H, d, J=2.7 Hz, ArH), 7.70 (1H, dd, J=5.5 and 7.7 Hz, ArH); HRMS (ESI) calcd. for C11H7FNO (M+H)+188.0506. found 188.0513.

Fuente