Reacción #2328993

Ecuación de reacción

2-(di-t-butylphosphino)-1,1′-binaphtyl

2-fluoroethanol

2-(di-t-butylphosphino)-1,1′-binaphtyl

Cs2CO3

2-(6-bromopyridin-3-yl)-6-methoxy-1,3-benzoxazole

2-Fluoroethanol

→

title compound

2-[6-(2-Fluoroethoxy)pyridin-3-yl]-6-methoxy-1,3-benzoxazole

Disolventes

EtOAc

Toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe mixture was again stirred 1 h at 120° C
2. 2
   TemperaturaThe reaction mixture was cooled to r.t.
3. 3
   Filtraciónfiltered through celite
4. 4
   Concentraciónconcentrated

Procedimiento

Toluene (1 mL) was added to Pd(OAc)2 (6.4 μmol), 2-(di-t-butylphosphino)-1,1′-binaphtyl (racemic, 8.0 μmol), Cs2CO3 (0.24 mmol) and 2-(6-bromopyridin-3-yl)-6-methoxy-1,3-benzoxazole under Ar. 2-Fluoroethanol (0.16 mmol) was added and the reaction was stirred 1 h at 120° C. Additional Pd(OAc)2 (8.0 μmol), 2-(di-t-butylphosphino)-1,1′-binaphtyl (racemic, 8.0 μmol) and 2-fluoroethanol (0.16 mmol) was added and the mixture was again stirred 1 h at 120° C. The reaction mixture was cooled to r.t., diluted with EtOAc, filtered through celite and concentrated. The crude product was subjected to reverse phase HPLC to afford the title compound as an off white solid (10.1 mg). 1H NMR (400 MHz, Chloroform-d) δ ppm 8.95 (d, 1H) 8.36 (dd, 1H) 7.62 (d, 1H) 7.12 (d, 1H) 6.91-6.99 (m, 2H) 4.82-4.88 (m, 1H) 4.69-4.76 (m, 2H) 4.61-4.66 (m, 1H) 3.89 (s, 3 H); MS m/z (M+H) 289.

Fuente