HCID 59404400, compound → HCID 59404394, compound

HRID 1873676Notes

Reaction equation

HRID 1873676 reaction equation
[C:1]1([C:13]2[C:14](=[O:28])[NH:15][C:16](=S)[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[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>CO.[Ni]>[C:1]1([C:13]2[C:14](=[O:28])[NH:15][CH2:16][C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[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

4

Reactant 1

HCID 59404400HCID 59404400, compound

Product 1

HCID 59404394HCID 59404394, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-5-thioxo-1,5-dihydro-pyrrol-2-one (4.7 g, 12 mmol) in MeOH (75 mL) under N2, with stirring, was added Raney nickel. The mixture was filtered under N2 and the filtrate evaporated. The residue obtained was purified by column chromatography (SiO2, EtOAc/hexanes), yielding 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1,5-dihydro-pyrrol-2-one as an off-white solid (2.2 g, 6 mmol, 51%). 1H NMR (400 MHz, DMSO) δ: 11.33 (s, 1H), 8.19 (s, 1H), 7.55 (s, 1H), 7.37 (dd, J=8.0, 6.0 Hz, 2H), 7.30 (d, J=2.8 Hz, 1H), 7.07 (t, J=7.6 Hz, 1H), 6.90 (t, J=8.0 Hz, 1H), 6.76 (d, J=6.4 Hz, 1H), 6.62 (m, 2H), 4.53 (s, 2H), 4.20 (t, J=5.6 Hz, 2H), 2.94 (t, J=5.6 Hz, 2H), 2.17 (m, 1H), 1.17 (m, 1H); LCMS: 354 [M+H].

Workup

  1. filtrationThe mixture was filtered under N2
  2. customthe filtrate evaporated
  3. customThe residue obtained
  4. customwas purified by column chromatography (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-efb41ebb424e4f2dbb2844d94611db31
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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