Indole-3-acetamide → 3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Participants

Reaction Steps

Compounds of the invention can be prepared according to the synthetic schemes described in WO 2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251, each of which is incorporated by reference in its entirety for all purposes. Briefly, the preparation of (±)-cis-3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione is prepared as a mixture beginning with the starting materials 1,2,3,4-tetrahydroquinoline and indole-3-acetamide. The 1,2,3,4-tetrahydroquinoline is converted into 5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl) oxoacetic acid methyl ester as described in Example 1, steps 1-5 of WO2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251. The 5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl) oxoacetic acid methyl ester is reacted with indole-3-acetamide as described in Example 1, step 6 of WO2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251, to yield 3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrole-2,5-dione. The mixture of (±)-cis-3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione is then prepared by catalytic hydrogenation as described in Example 2 using Procedure B of WO2006/086484, U.S. Pat. No. 7,713,969, and US 20100221251.

Provenance & Evidence