5-Methyl-7-(4-pyridyl)-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione → 5-Methyl-7-pyridin-4-yl-2-(2-quinolin-2-yl-ethyl)-1,2-dihydro-5H-pyrrolo[3,4-c]pyridine-3,6-dione

HRID 1752611Notes

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:5]2[C:15](=O)[N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[C:17](=[O:18])[C:4]2=[CH:3]1>C(O)(=O)C.[Zn]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)=[C:5]2[CH2:15][N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[C:17](=[O:18])[C:4]2=[CH:3]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-methyl-7-(4-pyridyl)-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione (60 mg, 0.15 mmol, see Example 4) and zinc power (28 mg, 0.4 mmol) in acetic acid (3 ml) was stirred at 110° C. for 3 hours. The solution was concentrated and purified by column chromatography on silica gel (EA:MeOH=5:1) to give the title compound as a white solid (23 mg, 40%).

Workup

concentrationThe solution was concentrated
custompurified by column chromatography on silica gel (EA:MeOH=5:1)

Sources & evidence

ORD record: ord-4cdad4c916454bc1939566d51c9b10a0
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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