Réaction #2328993

Équation de réaction

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

Solvants

EtOAc

Toluene

Conditions de réaction

Traitement

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

Mode opératoire

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