Reacción #11262

Ecuación de reacción

trimethylborate

amide

4-(2-Chlorophenyl)-6-methyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-ylformamide

tetrahydrofuran

→

( 922 )

Rendimiento 52.3%

4-(2-Chlorophenyl)-6-methyl-9-(methylamino)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Rendimiento 52.3%

Disolventes

Methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   Temperaturato warm to room temperature over 16 h
3. 3
   workup.STIRRINGthe reaction mixture was stirred for 12 h
4. 4
   OtroThe solvent was removed under reduced pressure
5. 5
   Lavadoeluting with petroleum ether:ethyl acetate (100:0 to 0:100)

Procedimiento

Borane methylsulphide complex (0.074 mL, 0.78 mmol) and trimethylborate (0.089 mL, 0.78 mmol) were added at 0° C. under an atmosphere of nitrogen to a solution of amide (920) (0.105 g, 0.26 mmol) prepared as described in example 469 dry tetrahydrofuran (10 mL) After stirring at 0° C. for 30 min. the solution was allowed to warm to room temperature over 16 h. Methanol (200 mL) was added and the reaction mixture was stirred for 12 h. The solvent was removed under reduced pressure and the yellow residue was purificatied by column chromatography on silica, eluting with petroleum ether:ethyl acetate (100:0 to 0:100) to give (922) as a red solid (0.053 g, 45%), mp 293–296° C. 1H NMR δ [(CD3)2SO] 11.01 (br s, 1H), 8.10 (d, J=2.3 Hz, 1H), 7.69 (s, 1H), 7.57 (dd, J=7.1, 2.0 Hz, 1H), 7.42–7.52 (m, 4H), 7.02 (dd, J=8.8, 2.3 Hz, 1H), 5.61 (q, J=5.2 Hz, 1H), 3.90 (s, 3H), 2.81 (d, J=5.2 Hz, 3H). EIMS found: M+=389.0929, 391.0905. C22H16ClN3O2 requires 389.0931, 391.0902.

Fuente