HCID 59408990, compound → HCID 59409007, compound

HRID 1894729Notes

Reaction equation

HRID 1894729 reaction equation
[C:1]1([C:13]([C:15]2[C:16](=[O:30])[NH:17][C:18](=[O:29])[C:19]=2[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:14])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[H][H]>O1CCCC1.[Pd]>[C:1]1([C:13]([C@H:15]2[C@@H:19]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:22][CH:21]=3)[C:18](=[O:29])[NH:17][C:16]2=[O:30])=[O:14])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

5

Reactant 2

HCID 59408990HCID 59408990, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59409007HCID 59409007, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbonyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (500 mg, 1.26 mmol) and 10% Pd—C (300 mg) in anhydrous tetrahydrofuran (60 ml) was stirred at room temperature under 1 atmosphere of hydrogen gas for 1 day. The mixture was filtered through celite and evaporated to dryness. The residue obtained was purified by flash column chromatography (SiO2, 65% EtOAc in hexanes) to yield (±)-cis-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbonyl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione as a pale yellow powder (186 mg). M.p.=283-285° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.64 (s, 1H), 11.1 (s, 1H), 8.46 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.42-7.36 (m, 3H), 7.19-6.97 (m, 4H), 4.85 (dd, J=5.0 and 46 Hz, 2H), 4.27-4.15 (m, 2H), 2.98-2.88 (m, 2H), 2.18-2.08 (m, 2H); LCMS: 398 [M+H].

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated to dryness
  3. customThe residue obtained
  4. customwas purified by flash column chromatography (SiO2, 65% EtOAc in hexanes)

Sources & evidence

ORD record
ord-68aec45da12b4b08b0392940a8208ab4
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

Loading…