Reaction #2328993

Reaction equation

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

Solvents

EtOAc

Toluene

Conditions

Workup

1. 1
   workup.WAITthe mixture was again stirred 1 h at 120° C
2. 2
   TemperatureThe reaction mixture was cooled to r.t.
3. 3
   Filtrationfiltered through celite
4. 4
   Concentrationconcentrated

Procedure

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.

Source