反応 #2328993

反応方程式

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

溶媒

EtOAc

Toluene

反応条件

後処理

1. 1
   workup.WAITthe mixture was again stirred 1 h at 120° C
2. 2
   温度The reaction mixture was cooled to r.t.
3. 3
   ろ過filtered through celite
4. 4
   濃縮concentrated

実験手順

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.

出典