Reacción #69001

Ecuación de reacción

2,6-difluoro-pyridin-3-ylamine

DMF

K2CO3

4-dimethylamino-benzoic acid

→

[4-(5-fluoro-oxazolo[5,4-b]pyridin-2-yl)-phenyl]-dimethyl-amine

Rendimiento 44.0%

Disolventes

pyridine

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe reaction mixture was concentrated
2. 2
   Otroaffording a residue that
3. 3
   workup.ADDITIONwas added in one portion
4. 4
   Concentraciónthe reaction mixture was concentrated to dryness
5. 5
   Otroaffording a residue to which
6. 6
   Filtraciónafter which the resulting mixture was filtered
7. 7
   Concentraciónconcentrated
8. 8
   Otropurified by silica gel flash chromatography (0 to 100% EtOAc in hexanes)

Procedimiento

To a solution of 4-dimethylamino-benzoic acid (635 mg, 3.84 mmol) in CH2Cl2 (38 mL) was added 1-chloro-N,N-2-trimethylpropenylamine (0.51 mL, 3.84 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (7.8 mL) before 2,6-difluoro-pyridin-3-ylamine (500 mg, 3.84) was added in one portion. After an additional 1 h, the reaction mixture was concentrated to dryness affording a residue to which was added DMF (5 mL) and K2CO3 (531 mg, 3.84 mmol). The resulting mixture was heated by microwave to 150° C. for 10 min, after which the resulting mixture was filtered, concentrated and purified by silica gel flash chromatography (0 to 100% EtOAc in hexanes) to afford [4-(5-fluoro-oxazolo[5,4-b]pyridin-2-yl)-phenyl]-dimethyl-amine (430 mg, 1.67 mmol, 44%). ES MS (M+H+)=258; 1H NMR δ (ppm)(DMSO-d6): 8.28 (1H, dd, J=8.36, 7.14 Hz), 8.01-7.94 (2H, m), 7.24-7.18 (1H, m), 6.87 (2H, d, J=8.89 Hz), 3.05 (6H, s); HRMS m/z 258.1039 (C14H12FN3O+H+ requires 258.1037).

Fuente