Reacción #163239

Ecuación de reacción

2-chloro-3-methoxy-5-nitro-pyridine

{4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester

potassium carbonate

→

title compound

{4-[4-(3-Methoxy-5-nitro-pyridin-2-yl)-phenyl]cyclohexyl}-acetic acid methyl ester

Disolventes

DME

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe crude reaction mixture
2. 2
   Concentraciónwas then concentrated in vacuo
3. 3
   LavadoElution with 30% EtOAc/hexanes

Procedimiento

To a solution of 2-chloro-3-methoxy-5-nitro-pyridine (0.10 g, 0.53 mmol, 1.0 equiv) and {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (0.2 g, 0.56 mmol, 1.05 equiv) in 5 Ml DME was added 0.5 Ml saturated potassium carbonate solution and 10 mg Pd(PPh3)4 catalyst. The reaction was heated to 100° C. for 2 h. The crude reaction mixture was then concentrated in vacuo and then loaded directly onto a silica gel column. Elution with 30% EtOAc/hexanes afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.19 (m, 2H) 1.15 (d, J=13.14 Hz, 1H) 1.46-1.59 (m, 1H) 1.51 (dd, J=112.38, 2.78 Hz, 2H) 1.81 (d, J=5.56 Hz, 4H) 2.26 (d, J=6.82 Hz, 2H) 3.61 (s, 3H) 4.00 (s, 3H) 7.36 (d, J=8.34 Hz, 2H) 7.90 (d, J=8.34 Hz, 2H) 8.20 (d, J=2.02 Hz, 1H) 9.05 (s, 1H); (M+H)+385.1.

Fuente