Reacción #68946

Ecuación de reacción

Tin (II) chloride dihydrate

N-(4-methoxybenzyl)-2-bromo-5-nitropyridin-4-amine

→

title compound

Rendimiento 88.1%

N4-(4-methoxybenzyl)-6-bromopyridine-3,4-diamine

Rendimiento 88.1%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónbefore being concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was suspended in a mixture of ethyl acetate and saturated sodium bicarbonate solution
3. 3
   Filtraciónfiltered
4. 4
   LavadoThe insoluble solids were washed with EtOAc
5. 5
   ExtracciónThe aqueous phase was re-extracted with ethyl acetate
6. 6
   Lavadothe combined organic layers were washed with brine
7. 7
   Secadodried (Na2SO4)
8. 8
   Concentraciónconcentrated

Procedimiento

Tin (II) chloride dihydrate (4.37 g, 19.4 mmol) was added portionwise to N-(4-methoxybenzyl)-2-bromo-5-nitropyridin-4-amine (1.31 g, 3.87 mmol) in absolute EtOH (10 mL) at room temperature. The mixture was then heated at 70° C. for 2 hours before being concentrated in vacuo. The residue was suspended in a mixture of ethyl acetate and saturated sodium bicarbonate solution and filtered. The insoluble solids were washed with EtOAc. The aqueous phase was re-extracted with ethyl acetate and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give the title compound as a brown solid (1.05 g, 3.41 mmol, 88%). 1H NMR (d6-DMSO, 400 MHz) δ 7.40 (s, 1H), 7.30 (d, 2H, 8.6 Hz), 6.90 (d, 2H, 8.6 Hz), 6.45 (s, 1H), 6.3 (br t, 1H, 5.5 Hz), 4.85 (br s, 2H), 4.3 (d, 2H, 5.5 Hz), 3.75 (s, 3H). LCMS (1) Rt=1.77 min; m/z (ESI−) 306, 308; (ESI+) 308, 310.

Fuente