Reacción #810594

Ecuación de reacción

(7R,8R,9R)-10-acetyl-8-(2-methoxyethoxy)-2-methyl-9-phenyl-7-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine

NBS

→

title compound

(7R,8R,9R)-10-Acetyl-3-bromo-8-(2-methoxyethoxy)-2-methyl-9-phenyl-7-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfterwards the reaction is quenched
2. 2
   workup.ADDITIONby adding of saturated aqueous sodium hydrogen carbonate solution and it
3. 3
   Extracciónis extracted twice with dichloromethane
4. 4
   LavadoThe combined organic layers are washed with brine
5. 5
   Secadodried over sodium sulphate
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe crude product is purified by column chromatography (ether/triethylamine: 95/5)

Procedimiento

To a of 0° C. cooled solution of 0.40 g (0.83 mmol) (7R,8R,9R)-10-acetyl-8-(2-methoxyethoxy)-2-methyl-9-phenyl-7-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine in ethanol (5 ml) is added 0.15 g (0.83 mmol) NBS and the mixture is stirred for 1 h. Afterwards the reaction is quenched by adding of saturated aqueous sodium hydrogen carbonate solution and it is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (ether/triethylamine: 95/5) to provide 0.30 g (0.53 mmol/65%) of the title compound as an amorphous solid. 1H-NMR (200 MHz, [D6] DMSO): δ=0.96 (s, 9H), 2.09(s, 3H), 2.42(s, 3H), 3.23(s, 3H), 3.40–3.53 (m, 2H), 3.69–3.98 (m, 2H), 4.23(t, 1H), 5.75 (d, 1H), 6.02 (s, 1H), 6.80(d, 1H), 7.16(s, 5H), 8.18(d, 1H).

Fuente