Reacción #170859

Ecuación de reacción

HOBT

1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid

DIPEA

octahydro-1H-pyrrolo[3,4-c]pyridin-1-one

EDC

→

title compound

5-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)octahydro-1H-pyrrolo[3,4-c]pyridin-1-one

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Otrothe solution was partitioned between water and 1:1 solution of ethyl acetate
3. 3
   ExtracciónThe organic extract
4. 4
   Lavadowas then washed with water (1×) and saturated aq. sodium carbonate (1×)
5. 5
   Secadodried with magnesium sulfate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroPurification
8. 8
   OtroResulting residue
9. 9
   Otrowas crystallized from the
10. 10
    Otroin vacuo removal of DCM

Procedimiento

The following was added sequentially to DMF (10 mL): 1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid (250 mg, 0.875 mmol), DIPEA (0.46 mL, 2.64 mmol), EDC (202 mg, 1.050 mmol), and HOBT (162 mg, 1.050 mmol). This solution was allowed to stir at rt for 1 h, at which time crude octahydro-1H-pyrrolo[3,4-c]pyridin-1-one (˜123 mg, 0.875 mmol) was added. Stirring continued for 12 h at rt, at which time the solution was partitioned between water and 1:1 solution of ethyl acetate:diethyl ether. The organic extract was then washed with water (1×) and saturated aq. sodium carbonate (1×), dried with magnesium sulfate, and concentrated in vacuo. Purification was accomplished via silica gel flash chromatography (100 g silica, 100% EtOAc.) Resulting residue was crystallized from the in vacuo removal of DCM to give the title compound as a slightly pink solid. (Yield: 200 mg, 0.49 mmol, 56%) 1H NMR (400 MHz, CDCl3) 7.72, 7.40-7.24, 7.20, 7.17-7.11, 6.94, 6.31, 5.51, 4.57, 4.30-4.08, 3.59-3.46, 3.39, 3.17-3.02, 2.63, 2.51, 2.02-1.77

Fuente